


Branching Out

by CLeighWrites



Series: Wincest Big Bang 2019 [1]
Category: Supernatural
Genre: Abusive John Winchester, Anal Fingering, Anal Sex, Being Broke, Big Brother Dean, Bisexual Dean Winchester, Coming Out, Dean Winchester Becomes a Hooker, Dean Winchester is Protective of Sam Winchester, Dean Winchester is Sam Winchester's Parent, F/M, First Time Topping, John Winchester Being an Asshole, M/M, Pre-Canon, Pre-Relationship, Prostitution, Protective Sam Winchester, Self-Doubting Dean Winchester, Self-Reflection, Top Dean Winchester, Vaginal Sex, Wincest Big Bang Prequel, Young Sam Winchester, pre-wincest - Freeform
Language: English
Status: Completed
Published: 2019-09-03
Updated: 2019-09-24
Packaged: 2020-10-06 10:35:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 23,017
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20505551
Author URL: https://archiveofourown.org/users/CLeighWrites/pseuds/CLeighWrites
Summary: Sam and John had been going at it for months. When it’s time for them to move, again, Dean steps in to take some of the brunt off his little brother. Things get physical, again, and this time Dean has had enough. The two of them leave John and finally branch out on their own. Dean finds out exactly what it’s like to support themselves and that he may need to seek alternative means of making money.





	1. Chapter 1

**Author's Note:**

> Since this is a prequel to my Wincest Big Bang there will be some wincestual feelings. It starts out the summer before Sam’s junior year in high school. Sam, 16; Dean, 20.

“This is bullshit, Dad, and you know it!” Dean was seething. 

“You watch your tone with me, boy.” 

John was a formidable man. Tall and muscular, but not in a body-builder sort of way. His short, dark curls made him look much more approachable than he really was, which Dean figured must have been good for his line of work. Dean had always known that whatever his dad was into wasn’t on the up and up, but he always had bigger things to worry about. His baby brother for starters.

Sammy had turned sixteen over the summer and was starting his junior year of high school in their current town of Poughkeepsie. John’s line of work kept them on the road quite a bit. Never staying in one place longer than six to eight weeks, and those times were only when John dumped the two of them off to fend for themselves for a while. 

Dean wanted nothing more than for his little brother to be happy. Make some friends, hell, maybe even get a girlfriend. Nothing brightened his day like seeing a smile on Sammy’s face. Those had been few and far between in the last few months as he and John had been fighting more and more. Dean had had to step in more than once to keep them from coming to blows. 

The most recent fighting was over moving again, just before school was scheduled to start. They had been holed up in an abandoned house just on the outskirts of town for almost four weeks. John had gotten a call to go vaguely west, but Sam decided that he wanted to stay, insisting that he was old enough and would emancipate himself if he had to. Sometimes, Sam was too smart for his own good.

Dean had been working doing oil changes and minor maintenance at an auto shop in town that didn’t ask any questions after Dean gave them the breakdown of a 502 big block without blinking. He’d been saving every penny he could so that he and Sam could finally leave John and live on their own. He only hoped the four hundred dollars he had on him would be enough, it looked like sooner was happening rather than later. 

“I’m twenty, now. I don’t need you to tell me what to do and where to go. I’m more than capable of taking care of myself… and Sammy,” Dean added, reluctantly.

“So, you think you’re such a big man now, is that it?” John stepped up to him and got right in his face. “What’s your plan, then, boy? You gonna change oil and fill washer fluid in soccer mom vans to support you and a teenage boy? You think that’s enough? You have no idea what it’s like to raise a kid, Dean. Hell, you’re still a damn kid yourself if you think you can.”

“Like you did any better!” Dean couldn’t help but yell back. “After mom, you went off the deep end.” There was a flash in John’s eyes, that was the only indication Dean got that he had struck a nerve. “I was only four years old and you had me taking care of Sammy! You don’t get to tell me that I don’t know how to support him and me, ‘cause that’s all I’ve known how to do my whole life!”

Sam came up behind him and put his hand on his shoulder to calm him down. A gentle, “Dean,” meant to break him away from their father’s deadly stare.

“If you think you’re so much better than me-”

“Oh, I know I am,” Dean interrupted him.

Before he knew what happened pain erupted across his face, starting at his left temple. Sam was pulling him away a millisecond later before throwing himself at the older man. Dean watched in awe as his little brother got two good swings in at their dad, forcing him to back down. 

Glad that they had already packed their bags before the fight broke out, Dean grabbed both his and Sam’s bags. He snatched the keys to their Impala and headed for the door.

“Come on, Sammy!” Dean yelled as he opened the door.

Sam was still breathing heavy, eyes on John daring him to make another move. Without turning his back on the man Sam made his way to Dean who reached out and grabbed his hand to lead him out of the house. Dean threw their bags in the back seat beside the already loaded cooler full of road food and jumped into the driver’s seat before John had made it outside.

“Don’t ever let me see either one of your faces again, you hear me!” John yelled from the porch as Dean peeled out and away from the dilapidated building.

Once they got a few miles down the road, and after his eye had mostly swelled shut, Dean pulled over and cut the engine. He took in deep stuttering breaths, trying to control himself. Never did he actually think he would be able to say those things to his father. He had always looked up to him, had always been a good son and done what he was told. However, he knew that he would do it all over again if it meant saving Sam from their dad. 

Dean’s knuckles were white, clutched tight on the steering wheel and Sam reached over with his own busted knuckles to pry them free, shushing him and telling him that everything would be okay. He hadn’t realized he was crying until he sniffled and went to speak. 

Sam slid closer to him and pulled Dean’s head into his chest, rubbing his hand through his hair to soothe him as he wept. “It’s okay… We’re okay… Thank you, Dean,” Sam comforted him.

They sat there, Sam holding him in the front seat of their only consistent home, on the side of the road until Dean could breathe steady again. He dragged himself out of his brother’s arms and muttered, “Thanks, Sammy. I’m sorry, I don’t know what that was.”

“You just did something terrifying and amazing. You were just getting through your nerves.”

“I just yelled some stuff and got punched in the face,” Dean countered. He reached down and grabbed Sam’s busted hand. “You’re the one that actually went up against him.” Dean was in awe of how brave his little brother had been. Even after everything that had happened, Dean doubted if he would ever have been able to throw a punch at the man.

“He punched you. I wasn’t just gonna stand there and let that happen,” Sam stated plainly, then added, “not again. I’m going to have to stitch you up.” The anger in Sam’s voice was almost startling, almost. Dean had hardly thought about what he must look like, it must be bad if Sammy thought he needed stitches.

“Hey, I’m the big brother, I’m supposed to take care of you.” Dean winced as he smirked at his little brother, then started the car.

“So, where to, now, big brother?” Sam laughed as he slid back over to his side of the car.

Dean thought for a second, then shrugged. “It’s getting kind of late. I guess we should find some place to sleep for the night. I’ve got some money saved up, we can look for a place tomorrow.”


	2. Chapter 2

**Summary for the Chapter:**

> Sam and Dean have left John for good. Dean is determined to be able to take care of his little brother, but realizes that he maybe his father had been right, and Dean is not ready to handle the responsibility on his own.

As it turned out, the motel they checked into for the night also had efficiency apartments on the upper floor. When Dean had asked the desk clerk for recommendations as he checked out, she had told him that they had a room available. Not wanting to push his luck, Dean prepaid for that weekend and the following week and happily took the key.

Sam looked at him curiously when he pulled into another parking space further down the row instead of pulling out of the parking lot. Dean simply wiggled his eyebrows and dangled the key from his fingers. “Home, sweet home.” 

Sam grinned at him and asked, “What number?”

“Lucky number…,” Dean flipped the tab on the key to read it, “21!” 

They got their bags out of the back of the car and made their way up the flight of stairs at the end of the building. Dean stopped at the door labeled ‘21’ and slid the key in, praying that it wouldn’t be a total dump. He held his breath as he opened the door and stepped in allowing Sam to step around him as he surveyed the room. It wasn’t much, but it was more than he was expecting.

On the far wall to the right, there was a short counter with a sink and a two burner stovetop that met up with a small refrigerator. There was a threadbare loveseat in the middle of the room that looked like it wouldn’t hold one of them, let alone both of them if they ever wanted to watch TV. Against the right wall, there was a small TV with an antenna on the top of it that didn’t inspire much confidence. Directly in front of the door was a desk and chair which led them into a small hallway with a door Dean assumed was the bathroom. 

Past that was the bedroom with the bed in the far right corner, a small bedside table on either side of it and a dresser on the opposite wall. Dean noticed with a pang that there were no linens on the queen bed and if he were to venture a guess, it would be that there also weren’t any towels, or dishes for them to use.

“Oh, man!” Sam yelled as he pushed past Dean and straight to the sliding glass door that Dean only just noticed led out to a semi-private balcony. 

This was a pretty decent room for the one seventy-five they were charging a week. Dean just hoped his remaining one hundred dollars would be enough to buy them some food and necessities until he got paid again. He was mentally calculating all the things they were going to need and approximating their costs when Sam came back in, a smile highlighting his entire face. 

“This place is great!” He stopped when he saw what must have been desperation on Dean’s face. “What is it?”

“Nothing, I just noticed; there’s no sheets or blankets. There’s probably no towels or dishes either. And we’re gonna need food, too.” Dean started reeling at all of the things he hadn’t thought about, maybe their dad was right. There was no way he could support Sammy on a minimum wage mechanic’s salary.

“Dean, hey.” Sam put his hand on his shoulder to grab his full attention. “We’re gonna be fine.” He smiled at him until Dean returned the gesture. “Um… how much money do you have left?”

“A little over a hundred. But I’ll need to put some gas in Baby for work. Man, maybe we should see if I can get my money back and look for a cheaper place.”

Sam looked around the room and seemed to really consider the space. “How much is this place?”

“One seventy-five a week. Including utilities.”

Sam nodded. “I don’t think we’ll find anything cheaper that’s this nice. I mean, for what all we’ve got here, that’s a good price. We can make it work.”

Once they decided to stay there, at least for the following week, Dean got to work unloading the cooler into the fridge. He had to use a dirty shirt to wipe out the dead bugs and dust from disuse, but they’d seen worse. Sam was unpacking their meager toiletries into the shower and medicine cabinet, then they both took their clean clothes and put them in their own drawers in the dresser, which had also been swept out with yet another dirty shirt. 

Dean took stock of their dirty clothes as well and decided that it would be cheaper to buy their own detergent. He shook his head, sat on the mattress and put his head in his hands. There was just too much that he needed to make sure Sam had. 

“Okay,” Sam said, walking into the room with a notebook. “What do we need?”

Dean took in a breath and looked up at him, marveling at how pragmatic his sixteen-year-old little brother was being. “Everything.” Dean shook his head feeling overwhelmed again.

“Specifically.” When Dean gestured vaguely to the entire apartment Sam huffed. 

“So far, I’ve got sheets, a couple of towels and washcloths, at least one pot and a pan, and a set of plates, bowls, silverware, and glasses.”

“Christ, Sammy. How the fuck am I gonna- Dad was right. I have no clue what I’m doing here.”

“No,” Sam defended. There was no malice in his tone, but Dean jerked anyway. “Dad was not right. You were. You’ve always been the one to look after me, make sure I had everything I ever needed. It’s not the best right now, but I can get a job and help out. We can do this, Dean; together.”

Dean’s heart swelled hearing Sam confirm all the things he’s always hoped were true. He did try his best, but he wanted so much more for Sam than he had ever gotten. “Alright, no chick-flick moments.” Dean cleared the emotion out of his throat. “Where can we go to get everything we need cheap?”

“We can start at a dollar store. After we fill up the Impala, that comes first.”

Dean smiled and nodded in agreement. He grabbed the keys off the desk and they headed out to spend the last of his savings. They got gas then headed to the nearest Dollar Tree.

There they were able to find their kitchen needs, as well as some canned goods. They picked out their own plates, bowls, and glasses; they realized if they were going to be cooking they would need utensils as well, so Dean grabbed a spoon, spatula, and a large knife, in addition to sets of silverware for them to eat with. 

Dean grabbed a pack of plain white kitchen towels as well, then went to look at the cleaning supplies. He grabbed a bottle of bleach, some glass cleaner, and dish soap. After he put the soap in the basket he realized that they would also need something to wash the dishes with; he added up what they already had and figured another dollar wouldn’t hurt anything. 

After they went through and got most of what was on their list, they went to the checkout. The older woman who rang them up seemed very sweet, probably concerned about the state of his face, and asked Dean if he had just moved away from home. Dean replied that he had and didn’t offer her any more information. 

Before they left, Sam turned around and asked, “Ma’am, do you know where another dollar store would be that has more household stuff? We just moved into town.” He smiled his most dimple ridden smile at her and she melted for him. 

She smiled and looked from Sam to Dean and back again. “Sure. Right on Arterial, left on White, right on Main, then left into the parking lot just past Gisselle’s Bakery.” She gestured with her hand, pointing out the direction of Arterial as she spoke.

Dean nodded his understanding. “Thanks.”

She gave Dean another look before she added, “You two watch out for each other.”

Dean turned back to her and gave her a smirk, “Always.” If there was one thing Dean was good at, it was taking care of his baby brother. 

They were able to find a bathroom set, complete with two towels, a bath rug, a shower curtain, and a set of washcloths. The Dollar General seemed to be the next level up from the Dollar Tree, having more of the bigger ticket things that they needed, but at a cheaper price than going to a bigger store. Dean was grateful that Sam somehow seemed to know where to go to get everything that they needed within their budget. They also found a pan and pot set, some detergent, as well as some more food to get them through until Dean got paid again. 

There was some debate about the bedding. Sam ended up winning, of course. He had argued that it made more sense to get the entire bed set as opposed to getting a couple of sheet sets and blankets separately. Dean didn’t know how it was going to work with them still sharing a bed for the foreseeable future. He had thought that they would switch out sleeping on the couch, but Sam was insistent. In the end they decided on a navy and cream colored set that came with everything they would need. So they wouldn’t have to go without bedding, Dean had still grabbed another sheet set for when they needed to do laundry. 

Having spent almost all of Dean’s savings, but primarily getting everything that they needed, they loaded up the car with their spoils and made their way back to the apartment. After they got everything set up and put away, Dean had to admit that for one hundred dollars and two young, inexperienced guys striking out on their own for the first time, the place didn’t look too bad. He was pretty sure that the only reason it didn’t look like a total shit-hole was because of Sammy, but he wasn’t going to tell him that. 

Looking around at the place that they could call their own, Dean felt a warmth spread through him. For the first time in his life, Dean had accomplished something without his father giving him orders on how to do it. He had gotten a place to live, and all of the things that they would need to survive for the time being. He was taking care of his little brother, and Sammy was going to be okay. Dean could only describe the feeling as being proud.


	3. Chapter 3

**Summary for the Chapter:**

> Sam and Dean have left John for good. Dean is determined to be able to take care of his little brother, but realizes that he maybe his father had been right, and Dean is not ready to handle the responsibility on his own.

It had been a month, Dean’s eye had healed and the place was actually starting to feel like home. They had food in the fridge, dirty towels on the bathroom floor, and a jar for quarters on the kitchen counter to save for laundry days. Sharing a bed hadn’t turned out to be too difficult either, the queen mattress offering plenty of room for both of them. 

If Dean was being perfectly honest with himself, he had always slept better with Sammy in the same bed as him. Something about being able to reach out and touch him if something were to happen, not that it would anymore, had Dean sleeping soundly. He’d had to get creative about when he took care of his morning wood, but he and Sammy had never been that shy around each other; growing up in close quarters being how it was and all. 

To that point, Dean had managed to stay on top of the bills and things. Until Sammy had his first week back to school and needed more supplies than they had budgeted for. They were somehow living off of Vienna Sausages and Ramen Noodles, and Dean still had to pay next week’s rent. 

He had taken off early Sam’s first day of school so he could pick him up. They had celebrated with burgers, fries, and milkshakes. Dean regretted that now. His check was short twenty dollars, and he had spent their extra money from the previous week on that dinner. He didn’t have enough to buy real food and gas, let alone make the rent payment. 

Lunchtime Friday found Dean sitting with his head in his hands in the break room instead of eating; trying to think of a way to come up with the money they needed quick. Something that didn’t involve selling Baby. She may have come from their dad, but she was more Dean’s than she had ever been John’s. No way was Dean willing to part with her. He wasn’t quite that desperate, and if push came to shove, they may need her to sleep in.

Between John’s gigs, while crisscrossing the country, they had stayed the night in the car, but it had never happened more than two nights in a row and Sammy had been half the size he was now the last time they had needed to do that. Dean was pretty sure they wouldn’t be able to fit themselves, and all of their newly acquired housewares, in Baby if things came down to that. And if they did, Dean would only be proving his dad right about him, he can’t handle taking care of Sam like he thought he could. The mere thought was nauseating.

“What’s got your melons in a wad, boy?” Gary, a thirty-something family man who was the owner’s cousin, asked.

Dean huffed as he sat up straight to look the man in the eye and answer, “I’m short on my rent for next week.”

“You paying rent weekly?”

Dean nodded, “Yeah, I sorta took my kid brother and left our dad. The hotel we stayed at had an efficiency open up, so we grabbed it. I don’t think we can afford anyplace else.”

Gary nodded and gave Dean a weak smile. “Sounds to me like you can’t afford that place either. Probly be cheaper somewhere else. I can ask around, the wife knows a few people.”

“Thanks, man; but if I can’t pay by tomorrow, we gotta pack up and head out.” Dean breathed out his growing panic and shook his head. “I don’t know what I’m gonna do.”

“I’ve got your number. I’ll call if she knows someone that’s got something ready to move in now.”

Dean nodded but wasn’t hopeful. “Thanks, Gary.”

“No problem, happy to help.”

With that, Gary threw away his wrapper and bag from his takeout lunch and left the break room. Thinking he was alone, Dean steepled his fingers and rested his forehead against them. “Fuck!”

Someone clearing their throat behind him had Dean wheeling around in his seat. The look on Billy’s face at Dean’s reaction showed that he had clearly not meant to startle him; that didn’t stop Dean’s heart from pounding in his chest.

“Sorry, dude. I thought you knew I was sittin’ here.” Billy was one of the younger men that worked in the shop, only a few years older than Dean; he was the token stoner of the group. 

“Yeah, of course, you just surprised me is all.”

Billy leaned over his table conspiratorially and lifted his eyebrows. “You know, I know how you can make some decent money, pretty quick.”

“What do you consider decent and how quick? What’s the catch?” Dean couldn’t care less if it was borderline legal, he just needed some quick cash to get him through the week. 

“Pretty kid like you… a hundred.” Dean’s eyebrows shot up and he tilted his head waiting for the other shoe to drop. “Tonight.”

Dean couldn’t believe it. A hundred dollars would be more than enough to get him and Sammy through the week. Hell, he could even get some apples for Sam to pack with his lunches. This was definitely too good to be true. “Ok, but what’s the catch? I ain’t robbin’ anybody for it if that’s what you’re gettin’ at.”

Billy grinned and shook his head, his hair falling into his face, blocking his eyes. “No stealing. It’s… mostly legal.”

“What exactly does mostly legal mean? Quit dicking around, what do I gotta do?” Dean was losing what little patience he had.

Billy checked the door and looked over his shoulder as if someone would be behind him, eavesdropping. “My cousin, Vinny-”

“Wait, wait,” Dean interrupted, failing at holding in his laughter. “You’ve actually got a cousin named Vinny?”

Billy looked confused, clearly not getting the joke. “Yeah, it’s short for Vincent.” He looked at Dean like that should clear everything up. “Anyways, my cousin Vinny runs this business.” He gave Dean a pointed look, like that was explanation enough.

“What kind of business,” Dean prodded. He really couldn’t afford to get tied up in some mafia shit when he had Sammy to think about, he was trying his best to be better than John, after all.

“Let’s just say he finds people… certain types of companionship.” He smirked and winked.

Dean’s stomach dropped. His cousin was a pimp. And Billy was suggesting Dean whore himself out for money. The thought had never crossed his mind. He couldn’t even believe he was half-way considering it. “Naw, man. That ain’t for me.”

Billy stood, throwing his trash away, preparing to head back into the bay area. “You don’t gotta make a thing of it, just tryin’ to help you get some decent money, dude. Give me a call if you change your mind.”

Dean stared at the door as it closed behind the man. Could he really bring himself to get paid for sex? He’d always said he would never pay for it, but this is literally the opposite. He liked a good night out as well as the next guy, would it be that different knowing he would be getting paid to be a sure thing? Would he actually be able to go through with it?

The answer was simple; yes. If it meant being able to provide for Sam, then, yes. Dean would do whatever it took to make sure his baby brother had everything he ever wanted. He was adamant about proving John wrong; he was more than capable of taking care of Sam. His entire life revolved around making sure Sam had everything he could possibly need, and when possible, anything he wanted. Even if that meant taking money for sex.

He laughed at himself and shook his head, figuring something else would come along and the idea of becoming a hooker would be a funny story he could tell Sammy later on. An interesting side-bar in their early days of being on their own.

****

Dean was cooking dinner when Gary called around seven and told him that his wife had a friend with an apartment over a corner store, but it wasn’t going to be finished for another two weeks. It was a studio, but it was only four hundred a month, much cheaper than renting by the week. 

Trying to remain positive, Dean told Gary to pass along the word that they would take it. He would figure out some way of making it through the next two weeks. He turned and looked across the room, watching Sammy study at the desk.

“Who was that?” Sam asked without looking away from his notes.

“Gary, from the shop. I was telling him about our place and he mentioned that he knew some people. He was calling to let me know that someone’s got an apartment that’ll be ready in a couple weeks.”

Sam turned to look at him, a dimply smile on his face. “Yeah? Can we afford it?”

‘Better than we can this place,’ Dean thought to himself. “Yeah, it’s monthly, but it’ll actually be cheaper than staying here. You gonna be able to say goodbye?” The joke earned a hearty laugh from his brother, which, in turn, had warmed Dean’s heart and made up his mind.

Sam went back to his homework and with a sigh and a sour taste in his mouth, Dean dialed Billy’s number.


	4. Chapter 4

**Summary for the Chapter:**

> Dean decides to meet with Billy’s cousin, Vinny to see about getting the extra money he needs in order to pay the bills and keep a roof over Sam’s head.

“So, uh, one of the guys at the shop invited me out tonight. You gonna be cool on your own?”

“I’m sixteen, Dean. I’m pretty sure I can tuck myself into bed.”

“Haha, smart ass. I just don’t know how late I’m gonna be.”

“You worry about me too much. I’ll be fine. I’m just going to finish up my homework, take a shower, then go to bed.”

Dean still didn’t feel right about leaving Sammy at night like this. It’s something John would do-- had done. Only difference was that he had left Dean with Sammy. Dean had never liked leaving his baby brother alone. “If you’re sure.”

“Dean, I’m fine. Don’t worry about me; go, have fun.”

“Okay,” Dean acquiesced, then realized Sam may not know how to get ahold of anyone if he needed to. “If you need anything, call Gary. His number is on the fridge.”

“With the number of the garage and the manager of the motel and that old lady that lives down the hall.” Dean let out an exasperated breath and looked Sam in the eye. He rolled his eyes and smiled up at him, dimples and all, then continued, “I’m going to be fine. Now, stop worrying and go have fun.” Sam stood and shoved at Dean’s shoulder, turning him toward the door.

“Alright, alright.” Dean turned around to give Sam one final look, more to reassure himself that he was doing the right thing. He wasn’t just abandoning his baby brother; he was going to make some quick cash so they could survive a couple more weeks until they could move. “Night, Sammy.”

“Night, Dean. See you in the morning.” 

****

Dean met Billy outside of a closed corner store, followed him around to the alley, and waited with him after he knocked on a rusted-over delivery door. Dean was feeling more and more like he had made the wrong choice. Then every time he thought of turning back, he was reminded that if he didn’t get some money, that he and Sam would have to pack up their lives into the Impala; Dean would not let that happen to his little brother. 

The door creaked open and Dean stepped back, not knowing what to expect. A man, with even oilier, shaggier hair than Billy, stuck his head out, looked both ways down the alley, then motioned for them to come inside. Billy went in first and Dean took in a deep breath knowing that nothing was going to be the same after this. 

The man led them down a hallway, checking over his shoulder to make sure they were still following him. “Billy wasn’t kidding. You are pretty.”

“Thanks, pal, but I don’t swing that way.”

The man stopped, turned, and stepped right up to Dean’s face. Dean swallowed, but stood his ground, checking quickly to see if the man had a weapon on him; a reflex from the training his dad had put him through. “Yeah, well, we’ll see about that.”

Dean sighed quietly when the man went back to leading them down another hallway. Billy was smiling and shaking his head. When they got to the end of that hallway the man opened a door and gestured for them to go in ahead of him. Dean never liked having people open doors for him like that, too many variables to consider if something went sideways. His senses were on overdrive and the last thing he wanted was to get locked into a room with the stoner guy from work with no way out and no idea where he was. 

Dean let Billy go first, again. When a light flicked on and Dean didn’t hear any other noises, he followed suit. They were in an office, an ornate solid wood desk took up a majority of the space, matching wood filing cabinets lined two of the walls, and a window behind the desk seemed to overlook a bigger, open room, like a warehouse. There were two captains chairs set at angles in front of the desk. 

Dean turned around when he heard the door shut behind him and the man was openly checking him out. He felt like a piece of meat. Dean shifted on his feet nervously waiting for someone to say something. 

With a laugh, the man held his hand out and introduced himself, “I’m Billy’s cousin, Vinny. Nice to meet you.”

“Dean,” he responded, taking the man’s hand in a tight grip; asserting himself the way John had taught him to. One of the good things that came from having him as a father. 

“Pleasure to meet you, Dean,” Vinny said, releasing Dean’s hand and walking around the desk to take his seat. He motioned for Dean to sit as well since Billy had already taken a seat.

“So, Billy tells me you need some quick money.”

It wasn’t a question, but Dean answered it anyway. “Yeah, I just need about a hundred to get me through the next week.”

Vinny smirked, looking over Dean like he was a piece of candy. “That can definitely be arranged. Are you sure you wouldn’t like to make this a more… permanent side job?”

“Naw, man. I’m just in a bind.” Dean wanted to be firm, but polite because this man was helping him out. “I appreciate the offer though.”

“Understood, but a pretty boy like you? You could make some real money.”

“I think I’m good, but thanks.” Dean was starting to wonder what was with these guys calling him pretty. Sure, he knew he was an attractive guy; he caught the eye of a lot of girls at all the schools he went to before he finally dropped out and got his GED, but pretty?

“That’s your decision, but you have an open invitation after tonight, assuming everything goes well. So, I have a few calls in from some regulars. I’ll give you the addresses and times. They will give you an envelope with payment. Don’t open them, you turn those into me at the end of the night and I give you your cut. Any questions?”

Dean only had about a million. “Yeah, um, these women just want sex, right? Like, nothing weird.”

“My clients have varied tastes, but since this is your first time out, I chose a few more… conservative clients for you.” He lifted his eyebrows, trying to gauge Dean’s reaction.

Keeping his composure, Dean continued with his questions. “So, I meet these girls at their place, we bang, then I take the money and run?”

Vinny laughed, “Yes, that is essentially what happens. Any more questions?”

Dean thought for a second, thousands of what-if scenarios rolling around in his head. “Um, will they have-” Dean stopped and shook his head, he never thought this was something he would have to ask anyone, ever. “Do they have condoms, or am I gonna have to go buy some?”

Vinny laughed at Dean’s naïveté, then reached into a drawer in his desk and pulled out a sleeve of condoms, tore a bunch off and tossed them toward him. Dean reached out, grabbed them and folded them into his pocket.

“Anything else, pretty boy?” Vinny asked.

Dean pursed his lips together and sifted through all the questions rolling around in his head. Most of them were about how he was supposed to act, things he was supposed to say or do as someone who was getting paid to have sex. He was good at reading people and figured that once he was in the situation, his instincts would kick in. “No, sir. I think I’m good.”

“Alright, then here you go,” Vinny said as he stood and extended his hand toward Dean. 

This time when Dean shook his hand, he received a piece of paper. When Dean flipped it over he saw times with addresses and first names next to them. So tonight Dean was going to be seeing Lisa, Anna, and Stacey. Billy stood and Dean followed him to the door as he tried to bolster his confidence.

“See you in a few hours, pretty boy,” Vinny called after him as he closed the door.


	5. Chapter 5

**Summary for the Chapter:**

> Dean heads out to meet his first ever clients and figures out how this whole hooker thing works.

Billy gave Dean directions to the first address since he still didn’t really know his way around town. Dean figured he could get whoever he was with to give him directions to the next place, or he’d just have to dig out the city map and find his own way. He was hoping this could be done quickly, so he could get back to Sammy. He hated having to leave him alone at night for so long. 

First stop was Lisa, she had a nice Craftsman style two-story house. It was painted in dark but welcoming colors; it was homey. He gave himself a moment to collect his thoughts before he got out of the car. _Just pretend like it’s a date; a date you know you’re going to fuck._ Dean shook his nerves off and made his way to the front door. It opened as soon as he knocked, which took him by surprise. 

“Took you long enough.” She told him as she grabbed his jacket and pulled him inside. 

“Sorry, sweetheart, didn’t realize I was on the clock.” Dean smirked at her and she seemed to relax. 

They both took a moment to look each other over. She was shorter than Dean, most people were, but he wouldn’t call her petite. She had long, dark, wavy hair, dark, tanned skin, chocolate brown eyes, and was wearing a simple cotton dress. She was gorgeous. She seemed to like what she saw in Dean as well and offered him her hand. 

She led him into the living room and sat down on the sofa, bringing Dean down right beside her.

“I don’t usually have the house to myself,” she said as she gestured to a photo of herself with a little boy. “My parents are in town, and they took Ben for the night, so I thought I’d make the most of it.” 

Dean nodded his understanding, “Well, if it makes you feel any better, I’ve never done anything like this before.” 

She laughed, but not in a cruel way, “You’re kidding me? Vinny sent me a newbie?”

Dean just shrugged, no sense in lying to the woman. “He’s helping me out.” Dean lifted his eyebrows suggestively, “So, uh, how do you want me?” He had to laugh at the absurdity of having to ask such a question, but he figured she’d know how to move forward more than he did, and she was the one paying for it anyways.

She smiled at him and put her hand on his thigh, she clearly wasn’t shy about what she wanted, and they both knew where this was heading. “You could start by kissing me.”

Dean felt a little like an idiot as he blindly followed her orders, but once his lips met hers, he let instinct take over. He quickly learned how she liked to be kissed and touched and handled. After only a few minutes of making out on the couch, Dean had her beneath him with her legs wrapped around his hips. She shoved his jacket off and reached for the hem of his shirt to pull it over his head. 

As he was sitting up between her legs, shirtless, looking at her laying out on the couch he had to ask, “Do you wanna do this here, or in your bedroom?”

“Here is fine,” she responded a little breathlessly, which made Dean proud. 

“Ladies choice,” Dean smiled and began to undo his jeans. 

While he was working on his pants, Lisa grabbed the hem of her dress and slid it over her head, leaving her bare beneath him. She was toned, Dean would have never guessed that she’d had a kid. Her breasts weren’t small, they weren’t huge either, but Dean still couldn’t wait to get his hands on them; he loved the feel of the soft pliant flesh in his hands. He had to keep reminding himself that he was getting paid for this; it wasn’t about what he wanted, it was about what she wanted. Dean had always been good about figuring out what girls wanted, though, so he wasn’t too worried about it. 

Once they were both naked, things moved along smoothly. Dean’s nerves, thankfully, didn’t affect his performance, and before too long Lisa was a sweaty, writhing, incoherent mess under him. She came, her entire body clinging to him like her life depended on it. She didn’t call his name or anything like that, and it made him feel a little weird about it. He didn’t have time to think about that too much, because her squeezing him so tightly made him thrust even harder into her until he was spilling his own release into the condom. 

Lisa didn’t seem to want to be held or touched now that she had gotten her rocks off, so Dean grabbed the end of the condom and pulled himself out of her. He felt awkward, not knowing his way around, or what to do or say at this point. He only stood there for a moment before Lisa sat up and grabbed her dress off the floor and put it back on. 

“There’s a bathroom under the stairs if you wanna clean up before you go.” She nodded behind him.

“Alright,” Dean responded lamely. 

He grabbed his clothes with one hand, still holding the condom secure with the other and stepped into the small half-bath. He plopped his clothes onto the toilet seat and removed the condom, throwing it into the trash can by the door. There was a washcloth folded and looking out of place on the sink, so he figured it was meant for him. He ran the water, splashing his face while it was still cool, then soaking the cloth in it once it was warm. He rinsed himself off as best as he could, then got dressed. He left the washcloth hanging to dry over the edge of the sink and then walked back out into the living room. 

Lisa was sitting in the chair by the window drinking a glass of wine when he stepped in. She smiled up at him, and held out an envelope for him to take. “Thank you, Dean.”

“You’re welcome?” Dean hated that it sounded like a question, but he really wasn’t sure how to respond. He’d never been formally thanked, let alone paid, for sex before. 

Lisa laughed it off, though. “I hope things work out for you.” She seemed earnest about it. 

Dean grabbed the envelope from her. “Me too, thanks. Um, have a good night.”

“You too, Dean.” Lisa went back to her glass of wine. 

Dean went to turn around then remembered that he didn’t know where he was going next. “Oh, um, actually. Do you know where Marshall Street is?”

She looked up at him, a little surprised that he would need to ask her for directions. “Yeah, it’s down Mansion off of Balding.” 

“Awesome, thanks.”

And with that Dean left Lisa sitting in her chair, drinking her wine, and walked back out to his Baby with an envelope full of cash. He was officially a hooker, prostitute, whatever you wanted to call it. He had had sex for money. But it was all for his little brother, so he couldn’t feel bad about it. 

_Next stop, Anna._

****

Anna had met him in the driveway of her house. Pulling him into a deep kiss as soon as he stood from his car. She was insistent, but not necessarily rough. Dean could respect a girl who knows what she wants. He balked when she opened the back door of Baby and started to climb in. But she was paying for it, so if she wanted some car sex, who was Dean to tell her no? Her driveway was overgrown with shrubs and trees on either side, so unless someone walked right up to the car, it wasn’t likely that they would get caught. 

They undressed each other between kisses and Dean felt a little like a teenager banging outside of her parents’ house, praying they wouldn’t walk outside. It was kind of fun, exhilarating on another level because he was here to do a job. Getting the condom out of his pants in the backseat of his car, with her lips on his neck had been more challenging than he would have expected. But once they got going, Anna wanted him to go slow, to take his time, really make her feel it. 

Dean had always prided himself on being able to give girls exactly what they wanted. If they wanted it rough, Dean would do his best, if they wanted it slow and smooth, Dean was happy to oblige; he’d never really had a preference, as long as she was happy. Partway through Anna nudged him to roll over, so he did, then she rode him until she could hardly hold herself up anymore, Dean only lasted a few more thrusts after he got back on top, and then it was done. 

Anna pulled a folded up envelope out of her pants’ pocket and tossed it in the front seat before giving him a quick kiss and leaving Dean flabbergasted in the backseat of his car. He watched as she walked up the steps to her house and slipped through the door. He had a good time, it had been a while since he’d had sex in the car, and it was a little more cramped than he had remembered it being, but he hadn’t expected to feel so… used. At least it hadn’t gotten awkward.

He got dressed quick and slid over the back of the seat to get behind the wheel, not wanting to make any noise with his creaky doors. Since Anna had hardly given him time to say anything, he pulled out his map and looked for a streetlight to park under so he could find his next address. It was right down the street a few blocks over. 

_Two down, one to go. Stacey, you’re up._

****

Stacey’s house was a large Colonial-style house. Grand, wide columns framed the front porch and there were even wrought iron lanterns hanging in front of either side of the door. Dean felt like he should be dressed better just to stand there. There was a doorbell outlined by a filigreed wrought iron cover beside the intricately decorated glass french doors. Dean shook his head at the ridiculous feeling he felt at being in this situation and pressed the button. 

A melodious tune played instead of the simple ding-dong he had expected to hear. He was suddenly very nervous. What if whoever came to the door was expecting some dapper dude in tails and a top hat. He felt very inferior, and the fact that he was being paid to be there to have sex with someone made him feel even less like he should be there. Just as Dean was starting to think that he should just leave and apologize to Vinny about leaving the job undone, the door opened.

There was little light coming in from behind them, but Dean could tell that it was a man who answered the door. He looked Dean over then said, “May I help you?”

He cleared his throat and introduced himself, “Hi, I’m Dean. Is, um, Stacey here?”

The man smiled at him then and opened the door further. “Yes. I’m Stacey, nice to meet you, Dean.”


	6. Chapter 6

**Summary for the Chapter:**

> Stacey helps Dean realize some things about himself

Dean’s blood ran cold. Stacey was a man. Vinny had sent Dean to have sex with some guy after he told him that he wasn’t gay. He tried to keep his expression neutral as he thought about how to get out of the situation without offending this man, who was clearly rich. 

“I can see that you were not expecting a man.” 

Shit, Dean chastised himself, you’ve already ruined it. “I’m sorry, I think there must have been some misunderstanding.” 

The man, Stacey, smiled at him and moved aside, gesturing for Dean to follow him into the foyer. He was in such shock that he didn’t think twice about following the man into his house. It wasn’t until he felt the man’s hand on his lower back, leading him into what must have been a sitting room, that he realized he had unwittingly agreed that this was going to happen. There had to be some way Dean could still back out gracefully, without ruining whatever he had going on with Vinny. 

“Look, um, mister-”

“Please, call me Stacey.”

“Okay, Stacey, I, um- I told Vinny that I don’t-”

“Do men? I know, he told me that’s what you said. He told me that you would more than likely, how did he put it? ‘Flip out’ when you got here. But he also told me that he thought that I might be able to change your mind.” One of his perfectly manicured eyebrows flicked upward at his last word and Dean felt legitimately flustered for the first time that night. 

Why would Vinny think that this man could change his sexuality? 

“You’re probably wondering why Vinny would have thought that I would be able to convince you to… switch teams.” Dean’s eyes went wide, it was like this man could read his mind. Stacey smiled, then continued with his explanation, “Let’s just say that Vinny has a sixth sense when it comes to people, and he knows that I have a way of getting people to see things in themselves that even they don’t know are there.”

“So you’re saying that Vinny thinks I’m gay and that you can get me out of the closet?” Dean was in shock, that was the most ridiculous thing he’d ever heard. 

“To put it bluntly. But you’re not gay, or you would already know that.”

Dean furrowed his brows, trying to think of what exactly this man was trying to say about him, but still maintaining some semblance of politeness. “Then what am I?”

“If Vinny is right about you, and he’s rarely ever been wrong, you’re bisexual. He sent you to me tonight to have me see if we could figure that out together.”

“Look, no offense, but I’m pretty sure I would know if I were into dudes.”

“Have you ever let yourself think about a man in that way?”

Dean rolled his eyes. “No.”

Stacey squinted at him, he seemed to be looking into his soul. It made Dean feel very uncomfortable. “You haven’t let yourself, or you haven’t wanted to?” Stacey’s voice was calm and soothing.

Dean took a second to really think it over. The only people Dean had ever really checked out had been girls. That wasn’t to say that he couldn’t tell when another guy was attractive, but that didn’t mean that he wanted to sleep with them. Did it? Dean thought back to locker room showers and wrestling meets and football games; had he ever felt anything sexual about those guys he thought were attractive? Dean shifted in his seat next to Stacey who was watching him with a genuinely curious gaze. Now that he thought about it, sometimes, sometimes, when he would jerk off after wrestling around and showering off with the guys in his class, he would think about how strong they were as they held him down, and how firm and smooth their chests were. But that didn’t make him gay, or bi or whatever. 

“Look, even if I maybe, sometimes, think about guys like that, that doesn’t mean that I wanna have sex with one.”

“That’s true, but if you’ve never really allowed yourself to think about it, how would you know?”

It was a valid question, Dean had never really thought about it because it was never really an option. He liked girls, and liked fucking girls, so why would he think about fucking a guy? “I don’t know, I guess.”

Stacey reached over and grabbed a glass off of a cocktail service tray and handed it to Dean. He held it out as Stacey regarded him, then picked a decanter from those that were there and poured Dean a drink. “You look like a whiskey man.” 

Dean didn’t respond. He downed the entire drink in one gulp and coughed as the alcohol burned his throat on its way down. Stacey laughed and refilled his glass. Dean took a small sip at it before speaking again. “Why does Vinny care if I know I like guys, or whatever, anyway? This is just a one time gig for me. Tonight, and we’re done.”

Stacey laughed again. “He said that’s what you thought, too. He’s pretty sure you’ll be back.” Dean looked at him, he could not believe that Vinny and Stacey had talked this much about him. Dean had known Vinny for less than ten minutes, what made him think that he knew him so well. “Don’t be upset. Vinny’s been doing this for a very long time. He’s very good at sizing people up, getting a good read on them.”

“So, Vinny thinks I’m good hooker material, good to know.” Dean rolled his eyes and took another long sip of whiskey, it was starting to hit him and he was settling into the conversation a little better now. 

“If it’s any consolation, I think you’re more than ‘hooker’ material. You’ve got spunk, Dean. You’re good looking, you’ve got confidence and charisma. In the right circles, you could really make an impression. If you wanted to, under the right circumstances, you could make a name for yourself, bring in some real money.”

That piqued Dean’s interest. “What do you mean?”

“I mean, Dean, you’ve got everything it would take to be a first-rate escort.” 

“Like, a fancy hooker?”

Stacey laughed and leaned into Dean’s shoulder when he did so. Dean was feeling tipsy enough that he didn’t think anything of it. “You’ve got a great sense of humor, as well. You would do marvelously at parties.” He leaned back to look Dean over again. “I’d love to see you in a suit. In fact, I’ve probably got one that would fit you. If you wouldn’t mind.” His question was implied.

Dean thought for a second, if he wasn’t going to have sex with this guy, the least he could do would be to put on a penguin suit. “Sure, why not?”

Stacey stood and held his hand out to help Dean off of the sofa. He didn’t need it, but he accepted the offer. He downed the rest of his whiskey, sat the glass on the service tray, then followed him down a wide hallway and up a rounded set of ornate stairs. They walked down what Dean guessed was some sort of breezeway, then Stacey opened a set of double doors. Lights came on automatically when they stepped into the room, Dean gaped at the size of the room. The efficiency he and Sammy were staying in could easily fit into this room. 

The far wall was all windows, covered by delicately flowing fabric; positioned on the right wall was the biggest bed Dean had ever seen, it was on a four-poster frame that had such detail carved into the wood, he wondered at how much that cost; there was a sitting area in front of a fireplace on the wall across from the bed and what looked like a hallway off to the left of that. Dean noticed that there were candles lit in the fireplace, offering the glow and effect of a fire without the heat. 

“Um, you usually just leave candles burning like that?”

Stacey turned to look at Dean before regarding the aforementioned candles. “I figured, one way or another, that I would end up in here, sooner rather than later, so there was no fear of an accidental fire breaking out.”

Dean didn’t respond, taking his time to really think about what Stacey was saying. If he wanted to he could leave. He didn’t have to be here. Now that they were in a properly lit space, Dean could get a good look at the man. He was dressed simply in a light grey pullover and slacks. Maybe his shirt was a little tighter than how Dean would wear it, but nothing looked really ‘gay’ about him. He was an attractive man, thick muscular arms and legs, nothing like Hulk Hogan, but he was in good shape. 

Stacey turned around and laughed, catching Dean staring at his ass. “Never really let yourself wonder, have you?”

Dean could feel his face catch fire. He looked around, they had taken the hallway into what was the size of another room, but was set up as a closet. An island in the middle held drawers and slots for shoes, the top of it littered with different accessories; the three walls held high shelves with hanging racks under them, full of clothes for all occasions and seasons. Coats led the way to jackets, which led to every color long-sleeved shirt that could be made, then onto more casual shirts and ended with matching slacks for each jacket, a few pairs of jeans, and a wide array of belts and ties, each with their own hook and place. 

Dean had never seen such a wardrobe before, how could one person need all these clothes. The most they had ever had was two pairs of jeans, five shirts, a few flannels, and a jacket each. Whatever could quickly be stuffed into a duffle at any given moment and be good enough. John had never been one for splurging on things that weren’t absolutely necessary. Dean reached out and felt the fabric of a soft-looking coat and marveled at how the material felt between his fingers. 

Stacey held a hanger out to him that had a pair of slacks, a crisp white shirt and a jacket on it. “Here, try this one. It should fit.” Dean took it from him and looked around for a place to change. Stacey smiled at him. “I’m not shy, you can change here.” 

Once again, Dean figured there was no harm in changing in front of the guy. He’d done it plenty of times in school, what made this time any different? He hung the hanger on the pole that Stacey had pulled up on the end of the island that seemed to be designed especially for that purpose. He kicked his shoes off, took off his jacket, then undid his pants. He figured he could give the guy a show at least, maybe then he’d still get paid. Dean smiled to himself as he grabbed the bottom of his shirt and turned while he lifted it over his head. He knew he had good looking back muscles, working under cars for years had given him a decent build. 

He worked his shoulders a little more than he normally would to take his shirt all the way off, then bent at the hips to take his pants off. He resisted the urge to turn around to see if he was affecting Stacey the way he thought he was. He slid the slacks off from the clothes hanger, unfolded them, then held them up to look at them before he decided that they should fit and bent back down to put his legs through. He left them undone and grabbed the shirt off the hanger and gave it the same treatment, the arms looked a little wide, but that wouldn’t be an issue, as long as the jacket fit well. He folded the bottom of his shirt the way his father had taught him before bringing the pants over it and fastening them, that way there were no lines or pulling on the shirt once it was tucked in. 

Checking himself over, he nodded then reached for the jacket, slipping his arms into the final piece before he turned around to face his host. Stacey looked like he wanted to eat him alive, so Dean knew he had done a good job at his striptease. That made him feel strangely proud of himself, and a little guilty since he still had no intention of sleeping with him. 

“Just as I thought.”

“I don’t look like an idiot in this thing?” Dean said a little self-consciously. He had never been in such an expensive fancy outfit before. The last time he could remember wearing anything close to this was the outfit someone had dressed him in for his mom’s funeral when he was four. 

“No, Dean. You don’t look like an idiot, but I was talking about that little show you just put on. You liked that didn’t you?”

Dean flushed at being called out like that. He’d never met someone so outspoken and just… blatantly honest. “Maybe.” Dean got a little hard at the praise and being openly asked about his performance. He liked knowing that people were watching him and getting off on it.

Stacey walked around the island and grabbed a bright, navy blue tie, then brought it to Dean, but when Dean reached out to take it from him, he shook his head. “Allow me.”

The man stepped right up to Dean, unfolded his collar, looped the tie around his neck and began to tie it. Dean felt flushed suddenly; after drinking a few fingers of whiskey, then putting on all those layers, and having some strange man dress him, Dean didn’t really know what was going on anymore. He felt lightheaded and as Stacey’s fingers fit the tie properly around his neck and straightened his collar, Dean felt a not entirely unpleasant feeling in his gut. He swallowed hard, and blinked his eyes, trying to get a grip on himself. 

“There you go,” Stacey said, his hands sliding slowly over Dean’s chest. He grabbed the lapels of the jacket and pulled them taut, causing Dean to step forward to keep his balance, which also put him even more in Stacey’s face. 

Dean looked from Stacey’s eyes to his lips reflexively. He reached out to put his hands on Stacey’s shoulders to steady himself and Stacey pressed himself closer to Dean. He could feel the solidness of the other man against him, and Dean felt himself reacting to the closeness. His cock started to swell more than it already had been. Was he really thinking about kissing this man? Stacey licked his lips. Dean was more than curious to know what they taste like, and before he knew what he was doing Dean was slamming their mouths together. 

It was strange to kiss a man, his lips weren’t as soft as Lisa’s or Anna’s had been, but that didn’t make them any less pleasant. Dean felt the stubble on Stacey’s chin rub against his own, and it drove him to deepen the kiss, slipping his tongue along the crease of Stacey’s until he opened up to him and he could kiss him properly. Stacey let Dean have control over the kiss, but started to walk him backwards until Dean’s back hit the wall or a closet door, he didn’t know, nor did he care. Dean was lightheaded, both from the drink and from the surprising arousal that came from kissing Stacey; the feel of his strong hands and lips exploring his body. It was a new and terrifying, but freeing and exciting feeling to be completely at the other man’s mercy; Dean surrendered.


	7. Chapter 7

**Summary for the Chapter:**

> Dean leaves Stacey’s and can’t stop thinking about what he’d just done

Dean stared at his steering wheel for what seemed like hours when he got into his car. He held his hands up in front of his face and studied them. Remembering what it had felt like to wrap them around another man’s cock, how tight and hot it had felt being knuckles deep in his ass. More importantly, Dean remembered how none of it felt wrong or dirty; it felt different, but in a good way.

Dean turned the key and felt the familiar rumble of Baby’s engine turning over; at the same time, he felt his dick twitch at the memory of Stacey wrapped tight around him, how his muscles had gripped him even tighter when he came. It wasn’t the same as being with a woman, for obvious reasons, but it was similar enough that Dean had gained his confidence fairly quickly once things had picked up. 

The entire drive back through town, Dean couldn’t stop thinking about everything that had happened. He replayed it over and over again, trying to figure out how he really felt about it.

_Stacey tugged on Dean’s bottom lip as he broke the kiss. He searched Dean’s face before sliding his fingers over the bulge growing behind the borrowed slacks. Dean groaned at the firm touch of the man’s long fingers and arched his back to get more friction. Stacey smirked at him, gave his cockhead a gentle squeeze, then backed away. _

_A whine slipped from the back of Dean’s throat, but any further protest was quelled by Stacey’s outstretched hand. Dean let Stacey lead him out of the closet and back into his massive bedroom. They stopped at the foot of the bed where Stacey took his time undressing Dean. He paid special attention to Dean’s nipples and hip bones, Stacey seemed to also enjoy feeling up Dean’s ass. _

_It wasn’t like Dean had never had his ass played with before, but there was something about the strength and size of Stacey’s hands that had Dean almost begging for more. More of what, Dean couldn’t really say; just more. Stacey gave Dean the choice, top or bottom; Dean still wasn’t sure exactly how things worked, but he knew he was good at fucking women, and how different could it really be to fuck a man? So, he chose top._

_After removing his own clothes, Stacey sat on the corner of the bed and pulled Dean down beside him. They kissed again until Dean’s body relaxed, then they laid down, and Dean let his hands roam. Stacey was hard between them and Dean felt the wet tip brush against his fingers as he moved his hand to grab Stacey’s hip. Stacey hummed and bucked his hips, rubbing his length into Dean’s hand._

_Dean only thought about what he should do for a split second before letting his instincts take over. He wrapped his fingers around the other man’s cock and began to stroke him. He alternated pressure and twisted his wrist until he found the exact way to stroke him that had him moaning and gasping. Stacey returned the favor, and Dean could swear that he had never been jerked off as good by anyone else before, not even himself. _

_It wasn’t too much longer before Stacey lubed up three of Dean’s fingers and guided them to his ass. He was laying flat on his back and had his legs spread, knees tucked up toward his shoulders. Dean had never seen a man spread out for him like this. He could see everything. Stacey’s dick, heavy and leaking on his belly, his bare balls hanging down leading to his clean-shaven asshole. _

_The pink, fleshy pucker was flexing, waiting for Dean’s touch. He knew the mechanics well enough, just like getting a girl ready for him, he’d have to work on the muscles, get them loose and pliant so Dean could get his cock in there. Of course, Dean also knew about a man’s prostate; not that he’d ever gone searching for one before, but he knew that would feel good for Stacey. _

_“Just start with one finger,” Stacey instructed. “You’ll feel how tight it is, when I loosen up, add another, then scissor your fingers.” Stacey wiggled his fingers in demonstration. “Don’t worry about doing anything else.”_

_Dean licked his lips nervously as he looked away from Stacey’s face and back down to where his fingers were hovering over his entrance. Stacey hissed in a breath when Dean finally applied pressure to his hole, the tip of his middle finger barely pressing in. He found his rhythm quickly, and before too long was fucking him with three fingers down to the knuckle. _

_One particular flick of his wrist and Dean felt a little bundle brush against one of his fingers, Stacey’s hips bucked and he moaned, fisting the sheets. Dean found the bundle again and rubbed against it deliberately, making Stacey arch off the bed and start to fuck himself on Dean’s hand. He couldn’t help the self-confident smirk that had spread across his face. _

_“Mmm, Dean!” Stacey yelled. Dean worked his fingers harder. “Oh, god! Dean, fuck me!”_

_Dean’s dick twitched and Stacey threw a condom at him when he eased up his ministrations. Stacey stroked himself while Dean slid his condom on and lubed up his cock. He had a moment's hesitation when he lined himself up, he looked to Stacey, who smiled and nodded at him to continue. Dean pushed but was met with such resistance he was sure he hadn’t prepped him enough._

_Stacey put his hand over Dean’s on his thigh and squeezed it. “It’s going to feel very tight at first. Keep going, once you get the head through, everything else will work out. It’ll fit, I promise.”_

_Dean had never had a pep talk during sex before, but it was kind of hot. It was almost painful on his tender head to shove against the tight ring of muscle so hard, but Stacey was right, once he got his head all the way in, and he felt that tight heat open up around him, it was like nothing he had ever felt before. He slid slowly all the way in, for the first time. Dean wasn’t one to brag, but he was rather large and no woman he had ever been with had been able to take all of him. _

_Having those hot, tight muscles flutter around his entire length was almost enough to make Dean come right away. He held his breath and focused on his hands on Stacey’s legs. Once he was sure he could handle it, he pulled out a little, the stretch and pull of skin around him was mind-blowing. Dean settled for short thrusts until he couldn’t stand it anymore and began to fuck into Stacey like his very life depended on it. Long, hard, deep thrusts that had his balls slapping against Stacey’s ass._

_Stacey was trying to meet Dean’s thrusts but gave up and just laid there while Dean fucked into him. Sometimes he would grab at Dean’s hands or his ass, sometimes his hands would run through and pull his own hair; Dean liked it best when his fists were white-knuckled into the comforter. His husky breaths and deep moans of pleasure drove Dean wild with want. _

_Women didn’t sound like that when he fucked them; Dean wanted to hear this man come apart beneath him. He knew when he found Stacey’s prostate and made sure to thrust at that same angle as often as possible. When Stacey started to squeeze even tighter around him, Dean saw his balls drawing up, so he wrapped his hand around Stacey’s cock and held it tight. On a deep thrust, Dean jerked him once, flicking his wrist just under his head, and Stacey came with a strained grunt. _

_The velvety constriction pulsing around him as Stacey came had Dean thrusting erratically until he finally shoved in deep and emptied his own release into the condom. Sweat was running down his face and his knees were shaking as he held the condom and pulled out. Stacey’s legs fell flat onto the mattress and his arms were covering his face. Stacey laughed._

_Dean’s heart sank for a moment until Stacey moved his arms and looked him in the eye. “There’s no way… you’ve never… fucked before, Dean. No one’s… that good… their first time.” He was breathing heavily and laughed again when he finished talking._

_“Well, I don’t know what to tell you.” Dean sat somewhat awkwardly on the end of the bed as he pulled the condom off. “Um, where-”_

_“There’s a trash can right here.” Stacey’s arm flung haphazardly toward the edge of the bed pointing vaguely beside the nightstand._

_Dean got up, walked over, and threw the condom into the decorative metal bin. As he turned to face the bed, Stacey gripped his hip and pulled him down to lay beside him. Dean had only ever snuggled like this with Sam when they had shared a bed when they were younger, and on more than one occasion as they got older, when there was no heat in the house. But it hadn’t been like this. _

_Dean had a fleeting thought about how nice it would have been if it had been. He shook the thought from his head and let Stacey burrow into his shoulder. Neither Lisa nor Anna had wanted anything to do with him after they had gotten off, so Dean wasn’t entirely sure what to do. He figured that Stacey was the one paying for it, so he’d let him drive. _

_They laid there until their breathing was steady, and just as Dean’s arm was starting to go numb Stacey stirred and sat up._

Dean shook his head and realized that he was parked down the alleyway where he’d met Billy and Vinny earlier that night. He took the wad of cash that Stacey had slid in his back pocket as he kissed him goodbye and shoved it into the glove box. Dean had given him a look and Stacey had just winked and told Dean he’d earned it, then he handed him the envelope for Vinny. He grabbed the other two envelopes of cash, locked the doors, and knocked on the door where he had met Vinny previously that night.


	8. Chapter 8

**Summary for the Chapter:**

> Dean has a productive and relaxing Saturday with Sam.

As soon as he got back to the motel, Dean took three hundred dollars and paid the night clerk for that week and most of the following week. He still couldn’t believe that he had made enough money for two weeks rent in one night. The extra cash Stacey had slipped him had been more than enough for what he needed. 

Dean tried not to think of it as easy money. He didn’t really want to go down that road. Now that he was caught up, and a little ahead, he would be able to save up for whatever they would need going forward. This was just a one night gig, he told himself.

He was quiet as he made his way through the small apartment and got himself ready for bed. He washed himself up with a hot washcloth before changing into a clean pair of shorts to sleep in. Sam mumbled and rolled over when Dean slipped between the covers, but stayed asleep. 

Dean’s mind was racing, but he forced himself to focus on calming, pleasant things to lull himself to sleep. He was exhausted, physically as well as emotionally, and within an hour of thinking of what sort of food he would be able to buy Sammy when they woke up, Dean fell asleep.

****

“Do we have the money for all of this?” Sam asked again while they waited in line. 

“Yeah, Sammy. I told you, we’re good. It’s not that much.” Dean hadn’t told Sam exactly how much money they had to spend, for obvious reasons; he didn’t want to have to explain where it came from. 

They got some fruits, pasta, different sauces, and some hamburger meat. Pasta was quick and easy enough to fix, and having different types of sauces to go with it, made it so that it didn’t seem like they were eating the same thing every night. They had sandwiches for lunches, and Sam would have some apples and oranges to take with him, and to snack on in the afternoons, Dean grabbed a bag of popcorn kernels.

Dean was tired, but was proud that he had figured out a way to pay their rent and get some more substantial food for his little brother. He would be damned before he let Sammy get scurvy. After they paid for their groceries they went to the movie rental store and got _Payback_, with Mel Gibson, and _Cruel Intentions_, because Sarah Michelle Gellar’s hot. 

After they ate dinner, Sam finished his homework for the weekend while Dean made some popcorn. He zoned out after pouring the oil and kernels into the pan and covering it with tin foil to keep the popped corn from shooting all over the living room. He thought about how much money he could make and what a better life he could offer Sammy if he worked for Vinny on the weekends. He let himself daydream of having movie nights more often and maybe even having a steak dinner once a week. Sam was a growing boy, he needed to eat more meat- - and veggies and pretty much, he just needed to eat more and better. 

When the popping became incessant, Dean removed it from the heat and pulled out their bowls. He split the popcorn between the two bowls and decided to put _Cruel Intentions_ in to watch first. Sam had said that it was based on a book he had read that Dean had never heard of, which wasn’t surprising. He figured if it was boring, and if they didn’t like it, they could swap it out for _Payback_, you could never go wrong with a good Mel Gibson, action flick. 

“Alright, Sammy. Ready when you are!” 

“I’m almost done with this chapter.” 

Within five minutes Sam joined Dean on the couch, their sides pressed together, and Dean hit the play button on the VCR. The music was pretty good, and Dean really liked the Sebastian character; he was a spoiled bitch, but Dean could sort of appreciate his sexual appetite, although not so much the urge to use sex as revenge and girls for conquests. Sarah Michelle was definitely hotter than the other girl, but the girl next door was always a better way to go over the uptown socialite. It was a little more of a chick flick than Dean thought it was going to be, but he caught himself rooting for Sebastian to get the girl. 

Dean almost choked on his popcorn when there was a long shot of Ryan Phillippe’s ass. He caught himself staring a little harder than he should have been; he glanced over to see Sam’s cheeks flushed and he nudged him to take the suspicion away from himself. Being pressed so tightly against his brother, and being flooded with the memories from the previous night, Dean was starting to get hard at the thought of Ryan being naked like that; he was a good looking guy. The entire rest of the scene Dean kept trying to figure out if he had actually put on a bathing suit, or if he was walking around in the pool comando. Knowing Sebastian, and what his motives were, he wouldn’t have put it past him. 

When they finally had sex, Dean had to shift in his seat to relieve the pressure in his pants. The movement must have caused Sam to get uncomfortable because he repositioned himself as well. It should have been more awkward to watch something so intimate with his little brother pressed right up against his side, but it was surprisingly comfortable. There was nothing that Dean could think of that he would do or say or watch where Sammy wouldn’t be welcomed company. They had always done everything together. 

Toward the end of the movie Dean coughed to cover his tears. When he glanced at Sam, he noticed that his cheeks were also wet, and didn’t feel so bad. 

“You deserve it, bitch,” Dean commented at the end when Sarah’s character was caught with her rosary full of blow. 

“Yeah,” Sam laughed in agreement. 

Dean leaned forward to rewind the tape and cleared his throat, “Okay, ready for _Payback_, or do you wanna go to bed?” It wasn’t too late, but Sam tended to keep to a fairly strict schedule, even on the weekends. 

Sam checked the time and nodded for Dean to swap out the tapes. “I think I’ve got another one in me.” 

Once the tape rewound, Dean switched it out for the other and hit play. Within forty-five minutes Sam’s head was on Dean’s shoulder and he was snoring softly. Dean was only half paying attention to the movie. He was a little preoccupied with how much older Mel Gibson looked. His hair wasn’t as long as it had been in the _Lethal Weapon_ movies, and he definitely wasn’t as young as he had been in _Mad Max_. He was still attractive though, and funny as ever in his rebel-without-a-cause sort of way. 

Dean was a little surprised at how easily he was letting himself notice how attractive the guys were in these movies. He had never really let himself think about it directly, but he must have noticed at some point in order to be having these thoughts. It was funny, looking back at how he’d thought about things before, compared to how he thought of them now. It was the same thought process, but more… honest? He enjoyed it more, he noticed. 

Before he knew it, the movie was over and he was trying to let Sam stay asleep on the couch for as long as possible while he shut the TV off, locked up, and put their dirty dishes in the sink; he would wash up the next day. Once he was ready to go to bed he knelt down and placed his hand on Sam’s shoulder, “Come on baby brother, time for bed.”

Sam jerked awake and yawned, “Oh, sorry. What did I miss?”

“Not much, we can finish watching it tomorrow. Come on,” he repeated as he grabbed Sam’s hand and pulled him upright. 

They brushed their teeth side-by-side with some effort, then got into bed. Sam was snoring again within minutes. Dean stayed up thinking about how mature Mel had looked, and how solid Ryan had looked with the water reflecting across his naked back. He had never fully lost his hard-on, with Sammy’s body heat keeping him warm and comfortable, so he decided that he would sleep better if he rubbed one off first. He folded the covers over and shoved his boxers down under his balls and started to stroke himself. 

He let pictures from his night with Stacey mix in with images from both movies he had watched and came up with his own fantasy that played out while he got himself off. He cleaned himself up with tissues from the nightstand, tucked himself back in, covered back up, and drifted off into a peaceful sleep. 

He never noticed that Sam had woken up beside him.


	9. Chapter 9

**Summary for the Chapter:**

> Dean and Sam move into their new place, things seem to be going smooth for a little while.

Dean was able to use what was left of his ‘hooker money’ and the following week’s paycheck to save up for a deposit on the studio apartment that Gary’s wife had found for them. Not having very much, they had moved in and set up everything within an afternoon. Dean had managed to borrow a futon from one of the guys at work until he could save up to buy a proper bed, or beds, for them. 

The kitchen was set up much the same way as it had been at the efficiency; everything was lined up against one wall. They were in a corner apartment, so two of the walls had windows that looked out over either street and let in plenty of natural light. The bathroom was tucked into the corner beside the kitchen, and there was a small linen closet along the same wall. During the day, they had the futon set as a sofa where they would sit to eat, and Sam could do his homework. They had yet to find a TV that was worth a damn and not too expensive, but they had a clock radio. 

Dean had taken to reading some of Sam’s books he had from past English classes to help pass the time. He especially liked The Outsiders. Something about a kid from the wrong side of the tracks trying to make it in the world struck a chord with him. He could also relate to Darry, raising his kid brothers, doing what work he could to get by. They had rented the tape after he and Sam had both finished the book; the soundtrack was great, and the cast was amazing, so many famous actors before they hit it big. Dean would never admit it to Sam, but he preferred the nuance the book had that the movie had missed out on. 

They also had some board games that had most of their pieces that they had scored at the local Salvation Army store. That was also where they had bought Sammy some new-to-him clothes since Dean’s hand-me-downs no longer fit his long limbs. Dean could wear Sam’s old clothes, so it worked out, even if he did have to cuff the pant legs. Anything to keep Sam from looking like a ragamuffin. 

****

Before Dean knew it, the sun was setting earlier and earlier, and the leaves had begun to turn; fall had settled in Poughkeepsie. Sam came home looking dejected one day, but wouldn’t tell Dean what was bothering him. He just shrugged it off and said that it was ‘nothing’ and that ‘it doesn’t matter, we can’t afford it’. After buying a bed, and a TV with a built-in VCR, Dean was starting to worry about saving up for rent again. He thought that Sam had everything that he would need, but maybe he had overlooked something. 

Since the studio was closer to Sam’s school, he would walk to and fro. Some days he would stay late at the library and spend time with a girl named Amy. Dean figured she was Sammy’s nerd girlfriend, no matter how vehemently Sam denied it. Most days he stayed late, he would come home with slightly swollen lips, mused hair, and a dopey grin on his face. Dean was happy that his little brother was in a place long enough to feel comfortable with a girl like that. Dean thought that maybe Sam’s surly demeanor was girl related, but he had no idea how to broach the subject with him. 

One afternoon, Dean had gotten off early and was busying himself before dinner by straightening up the clutter that had gathered during the week. While he was sorting through papers and mail on Sam’s desk, he found a permission slip for a field trip from Sam’s school; a form that Sam had never showed him. It was dated two weeks prior, and due the following week. It was for a ski trip in November. It would be for three days and included a two-night stay in a hotel in upstate New York. The price for each student was two hundred and fifty dollars, plus money for food and spending. _This must be what he said we couldn’t afford_, Dean deduced. 

Dean tucked the permission slip into his pocket and continued cleaning until it was time to start dinner. Just as he was about to pull the chicken breasts out of the oven, Sam stormed in. “Whoa, there, Sammy. Who lit the fire under your ass?” 

Sam threw his book bag under his desk and turned to face Dean. His face was beet-red, and it wasn’t from exertion. His cheeks were wet and his eyes were red and puffy. Dean dropped the pan of chicken on the stovetop and rushed over to him, grabbing him by the shoulders before pulling him into a tight hug.

“It’s Amy. She said that we can’t hang out anymore. Her mom found out why she’s been staying late at the library and flipped out on her. She won’t even talk to me, Dean!”

Sam was so pissed he was shaking, Dean shushed him and rocked him back and forth as they stood in what was their living/dining room. He was still upset but wasn’t crying anymore, having moved on from shocked, heartbreak to anger. Dean could still remember how he felt the first time a girl had gotten pissed at him before they had left town. It wasn’t a good feeling, and Sammy was much more tender-hearted than he ever had been. When Sam was breathing normally again, Dean slapped him on the back and walked back to the stove to finish their dinner. 

“Her mom is a psycho anyway. You dodged a bullet there, Sammy.”

“Yeah, I know, but I just- I thought that we- nevermind.” Sam sat dejectedly down on the futon and propped up their folding tables for them to set their plates on while they ate. 

“You thought that you’d move past the making out at the library stage of your relationship?” Dean tried to make it sound like a joke, but he knew he’d hit the nail on the head when Sam refused to look at him as he sat his plate down in front of him. “Look, Sam.” He set his own plate down and went back to the refrigerator to grab them some drinks. “You’re young, girls’ moms are way over-protective of them, especially bible-thumping ones like Amy’s. These kinds of things are going to happen. It’s nothing you did, and there’s nothing that you could have done to stop it.” Sam just nodded and poked at his chicken with his fork. “It’s not even that she doesn’t like you; this was probably just as hard on her as it was on you. She wouldn’t have spent the last two months playing tonsil hockey with you if she didn’t like you.”

Sam’s face flushed a deep red and Dean figured he’d broken through the hurt and put things in perspective enough for him to be able to work through the rest on his own. Dean knew first hand how crazy teenage hormones could be, how irrational they made people; even nerdy-smart ones like his baby brother. 

The following day, after Dean had thought about it and done some math, he realized that he was going to need to do something extra to get the money together for Sam to go on that ski trip. After everything that had happened with Amy, he needed something to look forward to. Also, after buying all the extra stuff they had needed for the apartment, Dean was more strapped for cash than he had anticipated and still owed the landlady their security deposit as well. She had been kind enough to let them make extra payments to cover that, but Dean knew that she was getting anxious about them being able to pay it off. He’d rather go ahead and be done with it.

He told Billy at work that day to let Vinny know that Dean would like to work the weekend if it would be possible, and Billy said that he would pass along the message. Being Thursday, Dean would be able to come up with a story to tell Sam and fix extra for dinner so that he could have leftovers one night, and not have to worry about making anything. Dean was making dinner and waiting for a phone call when Sam came in smiling and looking like he’d just won the lottery. 

“What’s gotten into you?” Dean asked him while he stirred the pasta and looked back at the phone on the wall. 

“Dean.” Sam’s voice was excited but serious. “I don’t want you to be mad.” 

_Oh, God, this isn’t going to be good_. “You didn’t get Amy pregnant, did you, Sammy? We’ve talked about-”

“God, no! Dean.” Sam’s face flushed and he stumbled over what to say next, how to get the topic off of his limited love life. Dean thought for a brief second that Sammy actually looked adorable when he got flustered like this. “I got a job.” He rushed out then turned away to unload his book bag.

Dean balked, that was not at all what he was expecting Sam to say. “You did what?”

“I got a job. I know that you’re stressed about money, and I don’t want you to feel like you’re doing this on your own. We’re in this together, and-”

“Sammy, I’m not-” the you-can’t-lie-to-me look on his brother’s face made him change his strategy. “I don’t want you to worry about that stuff. Your job is to go to school and be the super-nerd that you are. Hell, Sammy, you could get a full-ride scholarship to an Ivy League school if you want to. I never had that chance. My job is to take care of you. Don’t worry about me.”

“Someone has to. Dean, all you do is work and take care of me. You don’t even have a life. You’ve only ever been out with your friends from work that one time and that was months ago. I just… I feel like I’m ruining your life.” Sam almost whispered the last part. 

Dean’s heart broke. He had no idea that Sam felt that way. The last thing Dean ever would have wanted was for Sam to feel bad because of him. “Sammy. You have always been my life. Since I was four years old and I carried you out of that burning house. Taking care of you is what I do-”

“Do you know how fucked up that is, Dean?” Sam was getting upset, not what Dean had wanted to happen. 

“Look, I’m not saying that we’re not fucked up, and Dad-” Dean stopped and shook his head, John was a subject they rarely ever visited, and it never made either one of them feel any better. “I’m not saying we’re perfect, but you’re all I’ve got. And if I need to work a little harder to make sure you get the life you deserve, then that’s just the way it’s going to be.”

“But I can help, Dean. We’re in this together.” Dean was about to bite back when Sam added, “It’ll look better on college applications if I have work experience anyways.”

That made Dean stop and think. If having a part-time job would give Sam experience and look better for a college, that would be a good thing. Also, since Dean was planning on working a little more for Vinny, he wouldn’t have to worry about where Sam was or what he would do with himself. “Alright, Sammy. What’s this job?”

Over dinner, Sam told Dean all about the local Farmer’s Market and how they had a small grocery shop affiliated with them and that he had gotten a part-time weekend job stocking shelves and bagging stuff up for old ladies. It sounded like the perfect job for him; he was even excited about the green apron he had to wear. By the time Dean got the call from Billy to meet Vinny the next night, Dean wasn’t worried at all about what Sam would do while he was gone. And Sam was happy to know that Dean had plans to go out again and have fun with friends. Dean resolved never to let Sam find out exactly what he was up to on his weekends out.


	10. Chapter 10

**Summary for the Chapter:**

> Sam starts his new job and grapples with his teenage hormones and strange sexual urges (Sam’s POV)

Sam was enjoying his job. It felt good to work, to feel like he was making a contribution; to be able to give something back to Dean. Since before he could even remember, Dean had sacrificed everything for him. He was old enough now to take care of himself; and more than that, he could take care of Dean, too.

The main reason, other than money, that Sam had wanted this job was so that he would be out of Dean’s hair for a few hours and give him time to do something fun without having to worry about Sam being on his own. He hated feeling like Dean didn’t get to have a life because of him. This job helped him knock out two birds with one stone. He was quietly pleased that he had thought of it and that Dean had actually allowed him to work the job. 

It had been a couple of weeks, Sam had gotten two paychecks, and Dean seemed to be in higher spirits. He almost seemed happy. He was carefree in a way that made Sam’s heart ache for his brother. 

Their childhood had been so shitty, the only good thing about it, for Sam, had been Dean; and Sam had tried to make it as good for Dean as he was able. Laughing at his corny jokes, eating his God-awful, barely edible concoctions, and even trying to offer physical comfort when Dean was in a particularly bad way, snuggling in close late at night as Dean cried himself to sleep. 

Most kids their age would probably think it’s weird that they shared a bed; it wasn’t something Sam was going to bring up in conversation, anyway. The truth was, Sam had always slept better with Dean by his side. When the idea of them each getting their own bed for the new apartment had come up, Sam had argued against it. They were both too big for twin beds and there truly wasn’t room for anything more than that; so, Dean had bought another queen mattress so that they could keep using their same bedding from the efficiency. 

Another great thing about Sam’s job was that it was mundane and monotonous, which gave him plenty of time to think. He thought about other ways he could help Dean around the house, and about saving up to get him something good for their first Christmas away from their dad. He thought about the SATs and which college he’d like to go to, what he might like to major in; he thought about Amy, how unfair it was of her mom to take her out of school just because they had been dating behind her back.

His thoughts would always turn back to Dean again. How much happier he’s been since the move and in general since leaving John. How much more comfortable he is in his own skin. He seemed to be able to breathe for the first time in his life without the looming threat of their father to come and rip the rug out from under them.

Sometimes, on nights when Sam was feeling particularly horrible, he would think about the times he had lain in bed while Dean jerked off beside him, thinking that he was asleep. He knew it was wrong, but Sam couldn’t help himself; he loved the breathy little noises that Dean made, and the grunts he tried to smother with his fist. On more than one night, Sam had gotten himself off in the bathroom after Dean had started snoring. It didn’t feel wrong for him to think of Dean that way, although he knew that it should. They were brothers; they could never- 

Sam always stopped his thought process before he actually thought of what he would really like to fantasize about. It was best to not go that far, even with his thoughts. What would Dean think of him if he knew the sort of things he thought about? That was a risk Sam would never be willing to take. 

****

One day Sam decided to skip going to the library and head straight home; maybe he could get a head start on dinner and surprise Dean. He was hesitant to walk inside when he found the door already unlocked; he slowly pushed the door open and peeked inside. What he saw left him stunned.

Dean was sitting longways on the futon, legs spread wide, pants around his ankles, jerking off to porn on the TV. Sam had clearly interrupted Dean’s personal time. He fumbled trying to back out of the apartment and Dean’s face flushed when his head whipped up to find Sam staring at him from the doorway. 

Sam was too stunned to move; sure he had heard his brother rub one off more times than he could count, but to actually see it?

“You see something you like, Sammy?” Dean asked. He had pulled his knees up to try to recover some of his modesty, but his hand was still between his legs, and the porn was still playing on the TV. 

Sam could feel the heat from his cheeks spread as he tried to find a safe place to look. “Sorry! What? No.” He slammed the door shut by accident, his nerves too high to properly control his motor skills. “Shit, sorry,” Sam apologized again before dropping his bag by the door and all but running to the bathroom, slamming that door shut as well. 

Sam ran some cold water in the sink and used it to splash his face. Without prompting, his mind replayed what he had walked in on over and over again. Highlights being what Sam focused the most on; the pink flush to Dean’s pale skin, the way his freckles seemed to pop out even more, had that been gay porn he was watching? Unable to shake the arousal from his system, Sam decided that his best bet was to take a cool shower, give Dean enough time to- _no, Sam, that’s wrong_\- give _himself_ time to relieve some tension. 

Even the cool water wasn’t enough to calm Sam’s racing heart. He tried desperately to focus on the sounds of the running water and not to strain to hear what was happening in the other room. He had heard it enough to be able to imagine that he would hear Dean’s breath quickening, his needy moans the closer he got to finishing, the sounds of the two guys on the TV fucking the hell out of each other. Sam hardly had to stroke himself before he was spilling onto the bathtub floor. He watched his spendings flow with the water down the drain with a bad taste in his mouth; he’d let things go too far. 

He resolved to keep himself in check, but as the weeks passed by, he found himself walking in on Dean more and more. He even tried taking his time getting home, only to walk in the door just as Dean would be spilling into his hand, a surprised ‘Sammy’ making Sam’s blood boil. A part of him wondered if it was actually a mistake that Sam would catch him, or if he had planned it out that way, but Sam couldn’t let himself believe that Dean would want him to walk in on him jerking off. Sam had grown bold one night, and decided to jerk off in bed before he went to sleep; the next morning he woke up to Dean shaking the bed before challenging Sam to a race. 

It didn’t happen very often, but a few mornings a week, they would race to see who could come the fastest. Sam wasn’t exactly sure who won, thinking that the point should be to last the longest, but he never said anything to Dean about it. He kept those moments with him, refusing to look beyond the surface of two young guys, who happen to live (and sleep) together, who would occasionally fuck around and jerk off in front of each other. He’d heard guys in the locker room talk about circle jerks, what he did with Dean was sort of the same thing; even if they were brothers. There was no way Dean was as fucked up as he was, but they weren’t doing anything wrong.


	11. Chapter 11

**Summary for the Chapter:**

> Dean decides to keep working for Vinny, and Stacey surprises him with a new business opportunity.

Dean was beyond happy that he had managed to make more than enough money to send Sam on his ski trip as well as pay the rest of the security deposit and have the next month’s rent saved up. He really hated to think about it, but being a hooker wasn’t all that bad. He got to have more than enough sex to satisfy his needs, and he was making more money than he’d ever seen in his life. Granted, not all the sex was great, and some of the people Vinny assigned him to were really not his type, but Dean had developed a system for getting through those particular jobs. 

His jerk off sessions almost every morning and afternoon were helping him get better orgasm control. He could almost come on command; just thinking about it with minimal stimulation. Of course, he should have never involved Sammy. 

That first time Sam had walked in on him, watching gay porn of all things, had given him a thrill he never knew he’d craved. The flush of his brother’s face when he realized what was happening, and the adorable way he had gotten so flustered, then the shower he’d hopped right into; Dean could only imagine that he was jerking off in there. The thought should have turned his stomach, but all it did was make him come hard, all over his himself. 

The look on Sammy’s face when Dean handed him a check and the signed permission slip, more than made up for a few lousy fucks. He had, honest-to-God, tears in his eyes. He swore to pay him back and said that he would use his own money for food and spending while he was gone. Dean still planned on giving him some extra spending money, but for the most part, he let Sam have it his way. He was thrilled that his little brother seemed to be feeling better. He hadn’t seen Sammy smile that big in years, probably since Dean had snuck him out to a local county fair when he was about twelve or thirteen. 

Since Sam was working weekends, Dean decided that he could keep working with Vinny for a few more weeks; save up some money to give Sammy a really good Christmas, maybe even drive out to visit their Uncle Bobby. Dean smiled to himself, thinking about how much Bobby would appreciate them coming to visit. He could prove to him that leaving John wasn’t a big mistake, that Dean was more than able to take care of the two of them. 

Not that Bobby had ever uttered those words, but deep down, Dean wanted word of how well they were doing to get back to John. He'd also really just like to see him again; they hadn’t been out that way in a couple of years, and he missed the old man. Last time they had been out there, their dad and Bobby had gotten into it pretty bad. John had thrown some punches, and they had ended up leaving in the middle of the night. 

Bobby had been more of a dad to Sammy and him than John ever had, though. He’s the one that taught them how to play ball, and change out a transmission; Dean had snuck his first beer out of Bobby’s fridge. The more Dean thought about it, the more he wanted to make this a memorable trip; they had never been on a plane before, maybe they could fly out there, make it a real holiday. 

****

Fall was turning to winter in New York, and Dean was still working weekends with Vinny. It was the weekend before Thanksgiving, and Dean was pleasantly surprised to find Stacey’s name on his list for the night. He blew through the guys and girls on his list for that night, no pun intended; most of them were regulars, they would request him specifically, which was a source of pride for him. 

He found himself paying closer attention to the swoop of his hair and the state of his clothes as he walked up to Stacey’s door. He never noticed the strange car parked at the other side of the turnabout that was the driveway. He smiled as the door opened and blushed as Stacey hungrily looked him over. If he was completely honest with himself, that had to be his favorite part of the job; the unabashed way people would eat him alive with their gaze, he loved being admired like that. 

Stacey motioned for him to come in, and Dean followed him into the sitting-room they had talked in before. Dean was a little confused at first until he saw that they were not alone. Dean stopped in the doorway when a very hearty looking man in a very fine suit stood from the chair he had been occupying. The look on his face must have been comical because the man burst into laughter. 

“Stacey, I do believe we’ve scared the boy!”

Stacey turned then to find Dean stock-still at the entry to the parlor and joined the other man laughing. “My apologies, Dean, this is my good friend, Donald. I mentioned him in passing the last time you were here, and when I had heard that you were still working with Vinny, I thought that I should set up an introduction. Donald, this is Dean.”

Dean cleared his throat and stepped into the room, as he got closer to the man, he extended his hand and offered him a firm handshake. The man looked him right in the eye and tilted his head a little to get a different angle. It took him an embarrassing amount of time before he realized that this man must be the one that ran the fancy-hooker place Stacey had talked about; the reason he had tried on that suit that led to everything else that had changed Dean’s life that night. 

“Well, Dean, you are just as pretty as Stacey said you were.” The man, Donald, cut Stacey a look out of the corner of his eye. “Stacey is prone to exaggeration; however, I believe he may not have talked you up as much as he should have.” The man laughed again; he seemed to be a very jolly man, like Mr. Fezziwig from A Christmas Carol. “From what I’ve heard, you’ve got quite a talent, Dean.” 

Dean wasn’t sure how he should respond, so he looked from Donald to Stacey and back again. “Thank you?” He hated that it sounded like a question, but Dean still wasn’t really sure what was going on here. Was Stacey handing him off? Was this some weird sort of hooker espionage and this man was trying to steal Dean away from Vinny? “Um, no offense, Don, but- um, what’s going on here?”

Donald smiled at Dean and turned to Stacey. “You’re right; he’s got spunk.” He turned back to Dean and said, “Dean, my boy, Stacey thought that you would fair better on my side of this business, and I do believe he’s right. Personality and looks like yours are wasted working the trenches with someone like _Vinny_.” The way Donald spit Vinny’s name was almost like they were family. “My cousin-”

“Wait, Vinny is your cousin, too?”

“Too? Ah, Stacey mentioned that you were a mechanic, you must know Billy.” Dean nodded. “Billy is Vinny’s cousin on his mother’s side. I am Vinny’s cousin on our fathers’ side. They’re brothers.” 

Dean decided that he should call him Donny instead of Don, then pursed his lips and nodded, not caring about the familial ties, far more interested in what he had to do with it. “So, you wanna steal me away from Vinny; make me into a fancy hooker.”

Donald laughed at the term. “Dean, you are delightful! Stacey, I adore him. You thinking Wednesday night?”

Stacey smiled at Dean and kept eye contact with him as he nodded. “I think that would be a perfect trial run for him.”

Donald nodded his head like it had been decided. 

“Wait, just a minute. What’s Wednesday? What trial run? Don’t I get a say in this?”

“Dean, of course, you do,” Stacey answered, placing his hand reassuringly on his shoulder, the touch helping to calm Dean’s nerves. “Wednesday is the night before Thanksgiving, and a local socialite always has the most dreadful party to kick off the holiday season, as it were.” He shrugged and looked to Donald to finish the explanation.

“It’s never a good time, but no one can afford to say no,” Donald elaborated.

“So you think some boring, stuck up party is a good place for me to try out being a fancy hooker?”

Donald laughed again. “Oh, dear boy, I have a feeling that with you there, this will be the best little soiree this town has seen in the last decade!”

Donald and Stacey took the next thirty minutes to explain to Dean, in detail, exactly how the escorting business worked. Dean wouldn’t have to have sex for money, but it would be extra if he did. He would basically just be eye candy people took to parties and events where a date would be more acceptable than showing up stag. None of that bothered Dean, but what he was failing to understand was why it would be so much better for him. He didn’t mind having sex for money, the money was good, so why were they talking like not having sex would be so much better for him.

Dean cleared his throat to interrupt the current topic of clothes shopping and asked, “So, I have to get all new clothes-”

“At least one good, tailored suit, yes.” Stacey amended.

“So, I have to get a suit, and I don’t have sex with people, but I would get paid more if I did… why would this be so much better for me than sticking with Vinny?”

Donald gave Stacey a pointed look and nodded for him to answer. “Dean, just as an example, this party Wednesday night; it will only be for about four hours, there will not be any sex, and your share of the fee would be no less than six hundred dollars.” Stacey lifted his eyebrows and waited for the realization to sink in. “Tipping is also not frowned upon.”

Dean balked. He could make at least six hundred dollars… for four hours… and he didn’t even have to fuck anybody. It was a no brainer, he didn’t spare Vinny a second’s thought. “I’m in.”

Stacey and Donald both laughed again. They talked about times to take Dean to the suit shop and the timing of the party and when Dean should be where, then Donald left. Dean couldn’t resist grabbing Stacey by the face and kissing him hard as thanks for bringing him into this new world. Stacey led Dean by the hand up the stairs to his bedroom where Dean fucked him nice and slow. By the time Dean washed up and left to go back home, Stacey had come twice and gave Dean an even bigger tip than the first time along with his envelope for Vinny. Dean didn’t even feel bad when he told Vinny that he had what he needed and that he was done, ‘for good this time’.


	12. Chapter 12

**Summary for the Chapter:**

> Dean dives head first into escorting, and is able to surprise Sam and Bobby for Christmas.

Dean enjoyed being Stacey’s date to this socialite dinner party. He brushed elbows and made jokes with the upper crust, and in his new suit, they never suspected that he was a lowly mechanic from the other side of town. Men and women alike ogled him, and Stacey seemed to take pride in the fact that his date was ‘the most attractive man in the room’.

After Dean decided to spike the punch, the party went a lot smoother. Everyone relaxed, and conversation became much less stuffy; they actually seemed to be enjoying themselves. A few of the ladies had even suggested doing something called a ‘key party’. Stacey had to explain to Dean that meant that everyone who wanted to would put their keys into a bowl, then take turns pulling out a key, and that’s who they would go home with. It had been a popular practice in certain circles in the seventies and into the eighties, but by then swinging was more socially acceptable and the fad had died out. 

Dean figured these people really did need to let loose if they were suggesting swapping up based on keys in a bowl. Despite his recent background, Dean was less than thrilled at the aspect of a) putting the keys to Baby in a bowl, and b) having to go home with whoever pulled them out. Stacey assured him that if he were to go home with anyone, that it would be him, which helped to calm his nerves. Dean settled for turning the party into a real party, he subtly dimmed the lights and requested that the string quartet play something in a lower minor key, to set the mood. Stacey watched as he walked around the room, setting the scene. By the time Dean made his way back to him, he was barely containing his laughter. 

“You’re turning this party into a sex dungeon.”

Dean smirked and shrugged. “They wanna fuck, let them. They don’t need a fishbowl to do it.” Stacey looked at him like he’d just cured cancer. “Whaddya say we get this party started?” he asked, wiggling his eyebrows to further convey his meaning. 

“Do I have to pay extra for this?”

Dean laughed out loud, gaining looks from quite a few of the partygoers. “I’ll let this one slide.” Dean let his voice drop as he wrapped his fingers around Stacey’s neck and leaned into him so that he could slot their lips together. 

Stacey let Dean lead the kiss, to really put on a show for their onlookers. Dean bit into Stacey’s bottom lip and tugged, pulling the plump flesh through his teeth before it slipped free. He let his hands roam under Stacey’s suit jacket; Stacey returned the favor, letting his hands run down Dean’s back until they gripped his ass tight, thrusting Dean’s hips forward. Dean was once again greeted with a strange desire as Stacey’s fingers dug into the meat of his backside. Stacey was using the grip on Dean’s ass to rock them into each other. Neither one of them were able to contain their groans of pleasure as their erections smashed into each other over and over again. 

There was a responding moan from across the room, and the two men broke apart from each other long enough to see a man with a woman pinned up against the wall, one of her legs wrapped salaciously around his hip. It wasn’t much longer before everyone was paired off and in varying stages of foreplay. Dean figured his work was done, if that’s what his work was going to be, so he suggested that he take Stacey back to his place before it got too late. Stacey agreed on one condition; he wanted to top. After everything Stacey had done for him, and the feeling he got when his fingers were digging into his ass, who was Dean to deny him? 

****

Using some of the money he had gotten from Donald for the near orgy he had turned that pre-season social party into, Dean bought tickets for him and Sammy to fly out to spend Christmas with Bobby. He gave them to Sam as a surprise gift, which Sam almost didn’t open because it wasn’t Christmas yet. In the end, Sam had reluctantly opened them, then hugged Dean so tight he saw stars. He was proud of himself for being able to pull off such a gift for his little brother; not only did they get a trip, but they were flying and getting to spend time with the only person they could consider to be family for an actual Christmas. 

Dean discovered that he hated flying. He felt like he was going to die the entire way to Sioux Falls. Even Sammy holding his hand hadn’t been enough to calm his nerves. When he got off the plane, his legs were so shaky his knees were buckling, and Sam offered to find him one of the wheelchairs they used for the elderly and sick people. Dean had shoved him in the shoulder before pulling him back to him for support. 

They rented a car from the place in the airport and drove the rest of the way to Bobby’s. Sioux Falls hadn’t changed much in the few years since they’d visited last, and Bobby’s Salvage looked just like it had before; the maze of junk cars lining the dirt road that led to Bobby’s garage, and his neighboring house. Bobby had been his usual, surly self when they showed up, griping that they could have at least called to let him know they were coming. He could have gotten a pull out cot for them, made sure there was food in the house, the usual.

The old man couldn’t lie to them, though, he was happy to see them and to hear that they were doing so well on their own. Bobby had cut Dean an almost clairvoyant look when Sam had told him where they worked and that they had flown out to see him. Dean was sure that as soon as Sammy was out of earshot, he would get an ear full. Bobby was a little too intuitive for Dean’s liking; he’d have to think of a cover story, and fast.

Christmas was the best it had ever been. There were no skin mags wrapped in the funny papers, nor evergreen car fresheners hanging on the wall in the outline of a tree, and most importantly there were no stolen Barbie Dolls, which had been a terrible accident that _one time_ that Sam still made fun of Dean for. Sue him if he had tried to give Sammy a good Christmas, it’s not like their dad was going to do it for them. 

Bobby had a proper Christmas tree, with flashing lights and shiny ornaments, the whole nine. There were even a few things up there that he and Sammy had made when they were younger. Nothing fancy, just paper cut outs of their hands and weird little things Dean had made out of strung-together nuts and bolts. It worked; it was them. Dean blinked back tears at how much of them was still around Bobby’s house. He vowed that he would never let it go so long between visits again. John was gone from their lives; they could visit Bobby whenever they felt like it. There was no one to stop them, now. 

They made a spiral ham, mashed potatoes, and had cranberry sauce for dinner. Bobby had some homemade eggnog, which they drank as they watched _It’s a Wonderful Life_ on cable Christmas Eve. Bobby’s eggnog had some kick to it, and before too long, Sammy was dozing off on Dean’s shoulder, so Dean nudged him awake and told him to head to bed. Once Sam was upstairs, and Dean felt Bobby’s gaze on him, he decided that it was time to face the music. 

Without taking his eyes off the TV, Dean said, “Spit it out, Bobby.”

“What are you doing for money, kiddo?” The worry in Bobby’s tone was aggravating but in a comforting way. He knew Bobby only wanted what was best for both of them. 

“I work at an auto shop, we told you.”

“I look stupid to you, boy? I know how much a mechanic makes, and I know how much it costs to feed the two of you, not to mention, pay rent someplace.” Bobby’s voice was level, but still dripping with seething love. “Don’t make me ask you again, Dean. What are you doing for money… really?”

“Sammy’s got a job now, too.” He knew it wouldn’t work, and Bobby gave him a look which made Dean take in a deep breath, he’d thought about it, and decided to only mostly lie. “I work off the books on weekends.”

“Doing…?” Bobby prodded.

“Side jobs, people who don’t wanna take their car into a shop and pay those prices; I go to them, do what needs doing, they pay me, and that’s it.” Dean took another sip of eggnog to avoid looking Bobby directly in the eye. 

The old man was too good for Dean’s liking. He shook his head and leaned back in his recliner. “As long as you’re bein’ safe, and you’re not puttin’ yourself in any danger, I guess that’s what’s important.”

Dean had a feeling he wasn’t talking about having a jack give out on him in someone’s driveway, but didn’t acknowledge the distinction. “I’m just as safe as I always am. And I’ve got the money I need to make sure Sammy’s taken care of. _That’s_ what’s important.” 

Bobby pursed his lips together and nodded his head, then turned his attention back to the TV; the subject was dropped, and Dean didn’t feel too badly about not confiding in his father-figure. The last thing he wanted was judgment and ridicule, especially since he wasn’t going to be strictly fucking for money anymore. He’d only had the one escort gig, but he liked it much better than just being a hooker. 

****

The trip was pretty much a present for all three of them, but Dean had still made sure to get a little something extra for Bobby and Sammy to open on Christmas morning. He had grabbed a bottle of Johnny Walker Blue for Bobby while doing a grocery run, and had gotten Sammy and himself both two-way pagers. Since he was working, now, Dean would feel better if he had some way of getting in touch with him. Sam had surprised Dean with a gift as well, something he had picked up on his ski trip. He promised that it wasn’t much and that he didn’t have to wear it if he didn’t want to. That piqued Dean’s interest, and when he opened the package, he found a simple leather bracelet wrapped around and tied to itself. It was a black chord and was soft in his hand as he took it out of its box. 

Sam helped him to tighten it around his wrist after he slid it into place, and it felt like it was already a part of him. He swore to himself that he would never take it off if he didn’t need to. Sam rattled on about how the leather was hand-cut and dyed by some tribe in the region that handmade crafts and jewelry and other things that they had for sale at the resort his group had stayed at. Dean only half paid attention. He was glad that Sam had had a great time on his trip, even if he was a dork and learned something while he was gone. 

Since the trip had been a surprise, Bobby didn’t have anything for them. Improvising, he gave them each a twenty-five dollar gift card, Sam’s for Books-A-Million, and Dean’s for Sears. Dean was excited because Sears had some tools he’d had his eye on, and now he had an excuse to get them, even if he didn’t really need the gift card from Bobby to afford them. Sam was equally as excited about his gift card, that would be twenty-five dollars added to his own spending money to buy new books. If they weren’t careful, their entire apartment was going to turn into tool boxes full of books. As long as Sammy was happy, Dean couldn’t care less. 

Bobby gave Dean a sleeping pill to take for the flight back home, after giving him grief about being afraid of a little thing like falling out of the sky, which did little to help Dean’s nerves. When they got back home, Dean took Sam straight to the bookstore, where he spent his entire gift card as well as twenty dollars of his own savings. Most of his money was spent on a series about a wizard-boy who goes to wizard school and fights some Hitler sounding dude with his friends. It sounded cool enough, but Dean doubted he’d be borrowing those from Sam’s collection. 

All-in-all, Christmas was fantastic, and Dean couldn’t have hoped that it would have gone any better. Sammy was the happiest he had ever seen him, and they had been able to rebuild some old bridges that their dad had knocked down. That trip was just the vacation he needed before he moved on with his new plan. He was going to keep working at the mechanic shop, for appearances, but his primary source of income was going to come from escorting. He’d have to find some way of hiding the money from Sammy. Maybe he’d get Sam his own bank account, so he would have no reason to look into Dean’s affairs. Sam did have his own job, now, and since Dean wouldn’t really be needing his money to help pay for anything, Sam should keep it somewhere safe. 

With the partial lie he had told Bobby about side-work already set in place, Dean told Sam that he would be able to work more now that he had a job as well. He promised that he wouldn’t work too hard and that he would also take time for himself. Dean decided that with the escort work being mostly parties, he wouldn’t have to lie about hanging out with friends and going to parties; Sam would never know that he was getting paid to have a social life.


	13. Chapter 13

**Summary for the Chapter:**

> Sam is about to graduate and gets news about college; Dean does what he needs to and makes the necessary plans to move them across the country.

Sam felt like he was going to be sick. He sat in bed, the letter determining the rest of his life, clutched in his hand. He had read the first sentence so many times, he had it memorized. _Congratulations! It brings us great pleasure to welcome you to the graduating class of 2005!_ Stanford University. _Stanford_. Full-ride scholarship. California. Across the country. What would Dean think? Would he be happy for him? How was he going to live on his own on the other side of the country? _Stanford_! Sam was going to study pre-law at Stanford University. 

With so many thoughts running through his head, Sam never heard Dean come home. It wasn’t until he felt a warm familiar pressure on his shoulder, that he realized he wasn’t alone anymore. He jerked back to the present and looked up to his brother, silently holding out the letter for him to read. There was nothing to say, or to add to it. He waited for Dean’s reaction, not knowing how excited he would be allowed to feel about this amazing opportunity.

Dean was mumbling aloud as he read. “... welcome you to the graduating class of 2005! Sammy! This is amazing! Why are you not bouncing off the walls right now? Isn’t this what you wanted?”

Sam smiled and stood, accepting Dean’s hug. “Yeah, it is. Stanford’s a great school. It’s just… it’s in California, Dean.”

“And? What, you don’t wanna live where the weather is perfect year-round?”

“No, I’m sure that’s going to be great. It’s just… so far away.” Sam couldn’t bring himself to look at Dean for his reaction, so he grabbed the letter and walked over to the fridge to put it alongside the other acceptance letters he’d received. 

“Then would you rather go to Yale? I thought you were waiting for this one, Sammy? What’s the holdup?” Dean was starting to sound worried; the last thing Sam wanted. This was supposed to be happy news. 

“It was- is. I guess I’m just nervous about living across the country.”

“It’s not like it’ll be our first time in Cali. We’d been there a bunch… before.” Dean had become a master in ways to avoid mentioning their dad; it was a topic both of them had silently decided to never bring up, there was never a need to. 

“Yeah but- wait. Did you say ‘our first time’?” Sam smiled when Dean looked confused. “As in, you’ll be moving there with me?”

Dean flushed a little and rubbed the back of his neck like he did when he got nervous. “Yeah, I mean, Poughkeepsie’s getting old. I could use a little sunshine.” 

“Dean, you don’t-”

“Sammy, if you tell me I don’t have to do something for you, again… We’ve been through this.”

Sam knew that once Dean made up his mind about something, there was no getting around it. “But what about your job? Can we even afford it? How are we going to move our-”

“Tiny-ass, studio apartment half full of stuff across the country? They have these things called trucks. There’s even a company that rents them out, too. I thought you were the smart one, Sammy,” Dean teased. 

Sam huffed and rolled his eyes at his brother’s flippant attitude to uprooting his life. “And your job? All your friends? You’ve got a life here, Dean.” 

“I’m a mechanic, pretty sure they’ve got cars out in California; and I’m not worried about any of my friends. If I want to, I can always come visit. They’re not more important than my baby brother getting into _Stanford_!” 

Sam beamed at the praise. He was starting to lose the nerves he had built up in his head, and really let himself believe that it was going to happen. It wasn’t a possibility, or a pipe-dream, anymore. He was going to Stanford University. 

****

Donny was not happy to be losing Dean, but he did help get him hooked up with an agency out west. Apparently, Palo Alto was a rich-blood place, and very near San Francisco, which had a booming market for young male escorts. Dean was going to do just fine out there. 

Over the past year, Dean was able to save a considerable amount of money, and Sam never got suspicious about his activities. He was also able to store most of his wardrobe in a secret compartment in Baby’s trunk where his dad used to store his weapons. One good thing about John Winchester being a sketchy guy. 

Under Stacey’s advice, or rather, insistence, and Donny’s connections, Dean had started stripping for certain parties, in addition to attending events with clients. The two gigs never mixed, but around certain circles, people knew him from both of his roles. He had garnered quite a reputation for himself and was one of Donny’s most requested escorts. Of course, he still saw Stacey, whenever the mood struck him, and Dean was always happy to see his old friend. 

He would always be grateful to him; if it hadn’t have been for Stacey, Dean would have never allowed himself to entertain the idea of being with a man, and he never would have met Donny, who had opened doors Dean never would have dared to knock on. If it weren’t for Donny, the very concept of Stanford would be unfathomable. 

Donny introduced Dean to Benny, who was a ‘talent manager’ at the Palo Alto branch of the agency Dean would be transferring to. Within a month, Benny had found a house for Sam and him to move into, a tailor to make his custom outfits, and a mechanic shop that was hiring that Dean could work at. Everything was all settled. Benny was a Godsend. As far as he knew, everything was set for Sammy at Stanford, so all Dean had to do was wait for Sammy to graduate, pack up their meager belongings, and drive out west. 

****

On their last night in their studio apartment, they were watching a movie sitting on the futon mattress on the floor, everything else having been packed into the U-haul truck that was parked in the street outside. Dean noticed that Sam seemed to be sort of sad. It was probably the post-graduation, moving away from home, type of depression he had read about that some high school students go through before they leave for college. Also, the fact that they’d lived in the same place for almost two years, and now they were moving again couldn’t have been easy either. This was the first place that had ever felt like home to them. 

“What’s up Sammy?” Dean leaned into Sam’s shoulder. 

“Nothing, just thinking.” Sam leaned his head on Dean’s shoulder, and Dean shifted to tuck him under his wing. 

“Uh-huh. About what?” Dean pressed, the pamphlet he read said that getting teens to admit out loud about what they were feeling made the problem seem less scary, and talking things out with a trusted adult would help alleviate fears. 

“Just, moving and Stanford. What if…,” Sam stopped himself and buried his face into Dean’s side. 

His heart broke at whatever would make Sam feel so vulnerable. He thought for a second about not pushing him to talk more but remembered what the pamphlet had said. “What if what?” He rested his cheek on the back of his brother’s head and rubbed his hand down his arm, a comforting gesture that had always worked when he was younger. 

“What if I’m not good enough? What if moving all the way out there and going to Stanford is a bad idea?”

Dean leaned away from Sam and pulled him up so that he could look him in the eye as he responded. “There is no world where you are not good enough. You hear me? Sammy, you got a _full-ride_ to _Stanford_, you think they just give those out to anybody?” He pulled him into a tight hug that Sam reciprocated, and then added, “No way upgrading from Poughkeepsie to San Francisco is a bad idea, either.”

Sam sniffled and laughed. “It’s Palo Alto, Dean, not San Francisco.”

Dean ruffled his little brother’s hair, it had gotten so long in the past year that Dean had taken to teasing him for it, but couldn’t keep his fingers out of it. “It’s close enough,” Dean smirked and stood to go see what was left in the kitchen. “There’s nothing like eating comfort food, in bed, when you need comforting. It’s our last night here, let’s see what we’ve got.” Dean made quick work of a box of mac and cheese and the last of a pack of hot dogs, cutting them into tiny bites and mixing them all together. 

“Is there any ketchup?” Sammy asked before Dean had a chance to bring their bowls to their makeshift campsite for the night. 

Dean smiled to himself, remembering all the times he had tried to make simple mac and cheese a little more exciting to eat. Ketchup had always been Sammy’s favorite additive. He found a few packets still left in their ‘miscellaneous junk’ drawer and grabbed them with their bowls and a couple of spoons. “Sure thing, baby brother. Whatever you want.”

**Notes for the Chapter:**

> Thanks for reading! Don't be shy, let me know what you think!
> 
> Tune in for the Big Bang that this is a prequel for, Love, Lies, & Lap Dances! (Posting date in October tba)

**Author's Note:**

> Thanks for reading! Don't be shy, let me know what you think!


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